2-(Tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

Base Information

• Chemical Name: 2-(Tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid
• CAS No.: 166591-85-1
• Molecular Formula: C15H19NO4
• Molecular Weight: 277.32
• Hs Code.: 2933499090
• European Community (EC) Number: 675-754-2
• DSSTox Substance ID: DTXSID00570950
• Mol file: 166591-85-1.mol

Synonyms:166591-85-1;2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid;2-n-boc-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid;2-Boc-1,2,3,4-tetrahydroisoquinoline-1-carboxylic Acid;2-[(2-methylpropan-2-yl)oxycarbonyl]-3,4-dihydro-1H-isoquinoline-1-carboxylic acid;2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid;n-boc-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid;MFCD08274995;2-N-Boc-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid;R-(-)-2-Boc-3,4-dihydro-1H-isoquinoline-1-carboxylic acid;3,4-dihydro-1h-isoquinoline-1,2-dicarboxylic acid 2-tert-butyl ester;MFCD15474917;MFCD15474921;KMTRFKAFNRHBCH-UHFFFAOYSA-N;1,2(1H)-Isoquinolinedicarboxylic acid, 3,4-dihydro-, 2-(1,1-dimethylethyl) ester;2-[(tert-butoxy)carbonyl]-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid;SCHEMBL605316;DTXSID00570950;2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylicacid;AKOS010988285;AC-9206;CS-W003490;SB33807;SB33808;SB34149;DS-15274;SY021928;SY031356;SY233019;A3692;EN300-56243;Q-102318;Z852306810;(R)-2-Boc-1,2,3,4-tetrahydroisoquinoline-1-carboxylic Acid;2-(tert-butyoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid;N-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydro-1-isoquinoline carboxylic acid;N-tert-Butoxycarbonyl-1,2,3,4-tetrahydro-1-isoquinolinecarboxylic acid;(+/-)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid;1,2(1H)-Isoquinolinedicarboxylicacid,3,4-dihydro-,2-(1,1-dimethylethyl)ester;2-Boc-1 pound not2 pound not3 pound not4-tetrahydroisoquinoline-1-carboxylic Acid;2-N-Boc-1 pound not2 pound not3 pound not4-Tetrahydro-isoquinoline-1-carboxylic acid;N-[(1,1-Dimethylethoxy)carbonyl]-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

Chemical Property of 2-(Tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

Chemical Property:

• Vapor Pressure: 2.12E-08mmHg at 25°C
• Refractive Index: 1.556
• Boiling Point: 436.7 °C at 760 mmHg
• PKA: 3.49±0.20(Predicted)
• Flash Point: 217.9 °C
• PSA: 66.84000
• Density: 1.222 g/cm³
• LogP: 2.54340
• Storage Temp.: 2-8°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 277.13140809
• Heavy Atom Count: 20
• Complexity: 388

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydro-isoquinoline-1-carboxylicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC2=CC=CC=C2C1C(=O)O

Technology Process of 2-(Tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

There total 3 articles about 2-(Tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (41034-52-0) + di-tert-butyl dicarbonate (24424-99-5) → (±)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (166591-85-1)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

Reference yield:

1-isoquinolinecarboxylic acid (486-73-7) → (±)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (166591-85-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 59 percent / H₂ / PtO₂ / acetic acid / 24 h / 3102.89 Torr

2: 84 percent / aq. NaOH / 2-methyl-propan-2-ol

With sodium hydroxide; hydrogen; platinum(IV) oxide; In acetic acid; tert-butyl alcohol;

DOI:10.1016/S0223-5234(00)01206-X

Reference yield:

carbon dioxide (124-38-9,18923-20-1) + O-tert-butyl 1-(tributylstannyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (1359987-43-1) → (±)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (166591-85-1)

Guidance literature:

carbon dioxide; O-tert-butyl 1-(tributylstannyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate; With cesium fluoride; In N,N-dimethyl-formamide; at 100 ℃; for 3h; under 7500.75 Torr; Autoclave;

With hydrogenchloride; In diethyl ether; water; N,N-dimethyl-formamide; at 0 ℃; pH=2; Inert atmosphere;

DOI:10.1021/jo202597p

upstream raw materials:

1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

di-tert-butyl dicarbonate

1-isoquinolinecarboxylic acid

carbon dioxide

Downstream raw materials:

2-(tert-butyl) 1-methyl 3,4-dihydroisoquinoline-1,2(1H)-dicarboxylate

C₂₅H₃₂BrN₃O₄

1-(2,6-dimethyl-phenylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Refernces

• 1、 Mita, Tsuyoshi,Sugawara, Masumi,Hasegawa, Hiroyuki,Sato, Yoshihiro. "Synthesis of arylglycine and mandelic acid derivatives through carboxylations of α-amido and α-acetoxy stannanes with carbon dioxide". experimental part. p. 2159 - 2168. Retrieved 2012/06/01.
• 2、 -. "Polyfluorinated tripeptide thrombin inhibitors". . . Retrieved 2008/06/13.