tert-Butyl (3R)-3-(hydroxymethyl)morpholine-4-carboxylate

Base Information

• Chemical Name: tert-Butyl (3R)-3-(hydroxymethyl)morpholine-4-carboxylate
• CAS No.: 215917-99-0
• Molecular Formula: C10H19NO4
• Molecular Weight: 217.265
• Hs Code.: 2934999090
• European Community (EC) Number: 633-670-3
• DSSTox Substance ID: DTXSID40363823
• Wikidata: Q72503346
• Mol file: 215917-99-0.mol

Synonyms:215917-99-0;(R)-4-Boc-(3-Hydroxymethyl)morpholine;tert-Butyl (3R)-3-(hydroxymethyl)morpholine-4-carboxylate;(R)-4-Boc-3-hydroxymethylmorpholine;(R)-tert-butyl 3-(hydroxymethyl)morpholine-4-carboxylate;(R)-4-Boc-3-hydroxymethyl-morpholine;3(R)-Hydroxymethyl-4-Bocmorpholine;(R)-3-HYDROXYMETHYLMORPHOLINE-4-CARBOXYLIC ACID TERT-BUTYL ESTER;(R)-3-Hydroxymethyl-4-boc-morpholine;(R)-3-hydroxymethyl-morpholine-4-carboxylic acid tert-butyl ester;(R)-4-Boc-3-(hydroxymethyl)morpholine;MFCD06799477;SCHEMBL1184919;DTXSID40363823;BCP14804;3(R)-Hydroxymethyl-4-Boc-morpholine;AKOS015841592;AM84759;CS-W001900;DS-11385;A4640;EN300-159827;J-014161;tert-butyl (R)-hydroxymethylmorpholine-4-carboxylate;(3R)-4-(tert-butoxycarbonvl)-3-(hydroxymethyl)morpholine;(3r)-4-(tert-butoxycarbonyl)-3-(hydroxymethyl)morpholine;(R)-(-)-3-hydroxymethyl-morpholine-4-carboxylic acid tert-butyl ester;(3R)-3-(Hydroxymethyl)-4-morpholinecarboxylic Acid 1,1-Dimethylethyl Ester,99%e.e.

Chemical Property of tert-Butyl (3R)-3-(hydroxymethyl)morpholine-4-carboxylate

Chemical Property:

• Vapor Pressure: 2.53E-05mmHg at 25°C
• Refractive Index: 1.474
• Boiling Point: 320.708 °C at 760 mmHg
• PKA: 14.85±0.10(Predicted)
• Flash Point: 147.759 °C
• PSA: 59.00000
• Density: 1.118 g/cm³
• LogP: 0.55250
• Storage Temp.: 2-8°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 217.13140809
• Heavy Atom Count: 15
• Complexity: 224

Purity/Quality:

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

(R)-3-Hydroxymethylmorpholine-4-carboxylicAcidtert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCOCC1CO
• Isomeric SMILES: CC(C)(C)OC(=O)N1CCOC[C@H]1CO
• Uses: An intermediate of BMS-599626 An intermediate of BMS-599626, a selective and orally efficacious inhibitor of human epidermal growth factor receptor 1 and 2 kinases.

Technology Process of tert-Butyl (3R)-3-(hydroxymethyl)morpholine-4-carboxylate

There total 6 articles about tert-Butyl (3R)-3-(hydroxymethyl)morpholine-4-carboxylate 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: 82.0%

(R)-(4-benzylmorpholin-3-yl)methanol hydrochloride (714971-27-4) + di-tert-butyl dicarbonate (24424-99-5) → (R)-3-(hydroxymethyl)morpholine-4-carboxylic acid tert-butyl ester (215917-99-0)

Guidance literature:

With potassium phosphate; hydrogen; palladium hydroxide/carbon; In ethyl acetate; for 45h; under 775.743 Torr;

Reference yield: 82.0%

di-tert-butyl dicarbonate (24424-99-5) + (3R)-4-benzyl-3-(hydroxymethyl)-morpholine (101376-26-5) → (R)-3-(hydroxymethyl)morpholine-4-carboxylic acid tert-butyl ester (215917-99-0)

Guidance literature:

With 20% Pd(OH)2/C; hydrogen; In ethyl acetate; for 4h;

DOI:10.1021/jm9010065

Reference yield: 74.9%

di-tert-butyl dicarbonate (24424-99-5) + C8H19NO2Si → (R)-3-(hydroxymethyl)morpholine-4-carboxylic acid tert-butyl ester (215917-99-0)

Guidance literature:

C₈H₁₉NO₂Si; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 5h; Industrial scale; Green chemistry;

di-tert-butyl dicarbonate; With triethylamine; In tetrahydrofuran; at 20 ℃; for 24h; Cooling with ice; Industrial scale; Green chemistry;

upstream raw materials:

(R)-(4-benzylmorpholin-3-yl)methanol hydrochloride

di-tert-butyl dicarbonate

(3R)-4-benzyl-3-(hydroxymethyl)-morpholine

(3S)-5-oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid

Downstream raw materials:

(S)-tert-butyl 3-((4-(1-(3-fluorobenzyl)-1H-indazol-5-ylamino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-ylcarbamoyloxy)methyl)morpholine-4-carboxylate

[4-[[1-(3-fluorophenyl)methyl]-1H-indazol-5-ylamino]-5-methyl-pyrrolo[2,1-f][1,2,4]triazin-6-yl]carbamic acid (3S)-3-morpholinylmethyl ester

[(3R)-morpholin-3-yl]methanol hydrochloride

Refernces

• 1、 -. "DIHYDROPYRIMIDINYLTHIAZOLE FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION". Page/Page column 28. . Retrieved 2019/07/17.
• 2、 Gavai, Ashvinikumar V.,Fink, Brian E.,Fairfax, David J.,Martin, Gregory S.,Rossiter, Lana M.,Holst, Christian L.,Kim, Soong-Hoon,Leavitt, Kenneth J.,Mastalerz, Harold,Han, Wen-Ching,Norris, Derek,Goyal, Bindu,Swaminathan, Shankar,Patel, Bharat,Mathur, Arvind,Vyas, Dolatrai M.,Tokarski, John S.,Chiang, Yu,Oppenheimer, Simone,Hongjian, Zhang,Marathe, Punit,Fargnoli, Joseph,Lee, Francis Y.,Wong, Tai W.,Vite, Gregory D.. "Discovery and preclinical evaluation of [4-[[1-(3-fluorophenyl)methyl]-1H- indazol-5-ylamino]-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl]carbamic acid, (3S)-3-morpholinylmethyl ester (BMS-599626), a selective and orally efficacious inhibitor of human epide". supporting information; experimental part. p. 6527 - 6530. Retrieved 2010/03/26.