tert-Butyl (1,3-dioxo-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindol-2(3H)-yl) carbonate

Base Information

• Chemical Name: tert-Butyl (1,3-dioxo-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindol-2(3H)-yl) carbonate
• CAS No.: 64205-15-8
• Molecular Formula: C14H17NO5
• Molecular Weight: 279.293
• Hs Code.: 2925190090
• DSSTox Substance ID: DTXSID90538701
• Mol file: 64205-15-8.mol

Synonyms:64205-15-8;tert-Butyl (1,3-dioxo-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindol-2(3H)-yl) carbonate;Boc-ONb;tert-butyl (3,5-dioxo-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl) carbonate;2-[[(tert-Butoxy)carbonyl]oxy]-3a,4,7,7a-tetrahydro-4,7-methano-1H-isoindole-1,3(2H)-dione;SCHEMBL4445730;DTXSID90538701;tert-Butyl(1,3-dioxo-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindol-2(3H)-yl)carbonate;CS-0454519;J-513188;tert-butyl 3,5-dioxo-4-azatricyclo[5.2.1.0(2),]dec-8-en-4-yl carbonate;tert-butyl 3,5-dioxo-4-azatricyclo[5.2.1.0,dec-8-en-4-yl carbonate;2-[(tert-Butoxycarbonyl)oxy]-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione;Tert-butyl (1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-4,7-methanoisoindol-2-yl) carbonate;4,7-Methano-1H-isoindole-1,3(2H)-dione,2-[[(1,1-dimethylethoxy)carbonyl]oxy]-3a,4,7,7a-tetrahydro-;4-({[(2-Methyl-2-propanyl)oxy]carbonyl}oxy)-4-azatricyclo[5.2.1.02,6]Dec-8-ene-3,5-dione

Chemical Property of tert-Butyl (1,3-dioxo-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindol-2(3H)-yl) carbonate

Chemical Property:

• Boiling Point: 360.898 °C at 760 mmHg
• Flash Point: 172.065 °C
• PSA: 72.91000
• Density: 1.334 g/cm³
• LogP: 1.59810
• Storage Temp.: 2-8°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 279.11067264
• Heavy Atom Count: 20
• Complexity: 488

Purity/Quality:

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

Boc-ONb ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)ON1C(=O)C2C3CC(C2C1=O)C=C3

Technology Process of tert-Butyl (1,3-dioxo-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindol-2(3H)-yl) carbonate

There total 2 articles about tert-Butyl (1,3-dioxo-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindol-2(3H)-yl) carbonate 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:

N-hydroxy-5-norbornene-2,3-dicarboximide (21715-90-2) → (N-hydroxy-5-norbornene-2,3-diformylimino)tert-butyl ester (64205-15-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaOH / 1.) MeOH; 2.) benzene, 10-15 deg C, 2 h

2: pyridine / 1.) room temp., 1 h; 2.) 35 deg C, 3 h

With pyridine; sodium hydroxide;

DOI:10.1055/s-1987-27873

Reference yield:

Chlorameisensaeure-N-hydroxy-norborn-5-en-2,3-dicarboximidester (99502-89-3) + tert-butyl alcohol (75-65-0) → (N-hydroxy-5-norbornene-2,3-diformylimino)tert-butyl ester (64205-15-8)

Guidance literature:

With pyridine; 1.) room temp., 1 h; 2.) 35 deg C, 3 h;

DOI:10.1055/s-1987-27873

Reference yield: 91.0%

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + (N-hydroxy-5-norbornene-2,3-diformylimino)tert-butyl ester (64205-15-8) → N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4)

Guidance literature:

With tertiary amine; In 1,4-dioxane; water; for 3h;

DOI:10.1055/s-1987-27873

upstream raw materials:

Chlorameisensaeure-N-hydroxy-norborn-5-en-2,3-dicarboximidester

tert-butyl alcohol

N-hydroxy-5-norbornene-2,3-dicarboximide

Downstream raw materials:

L-N-Boc-Ala

N-tert-butoxycarbonyl-L-leucine

N-tert-butoxycarbonyl-L-phenylalanine

BOC-glycine

Refernces