Tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: Tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate
• CAS No.: 114214-69-6
• Molecular Formula: C10H19NO3
• Molecular Weight: 201.266
• Hs Code.: 2933990090
• European Community (EC) Number: 805-026-3
• DSSTox Substance ID: DTXSID60412261
• Mol file: 114214-69-6.mol

Synonyms:114214-69-6;1-Boc-3-hydroxymethylpyrrolidine;Tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate;1-Boc-3-(hydroxymethyl)pyrrolidine;3-Hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester;(S)-1-Boc-3-(hydroxymethyl)pyrrolidine;1-PYRROLIDINECARBOXYLIC ACID, 3-(HYDROXYMETHYL)-, 1,1-DIMETHYLETHYL ESTER;MFCD02179040;1-Boc-3-pyrrolidinemethanol;(R)-1-BOC-3-PYRROLIDINEMETHANOL;3-Hydroxymethyl-1-Boc-pyrrolidine;SCHEMBL621267;tert-Butyl-3-(hydroxymethyl)pyrrolidin-1-carboxylat;N-BOC-DL-BETA-PROLINOL;tert-butyl 3-(hydroxymethyl)-1-pyrrolidinecarboxylate;N-Boc-3-hydroxymethylpyrrolidine;DTXSID60412261;HKIGXXRMJFUUKV-UHFFFAOYSA-N;BCP22293;BCP27049;AKOS005264112;AC-3511;CS-W009119;PB23288;PB30747;PB33659;1-t-butoxycarbonylpyrrolidine-3-methanol;1-t-butoxycarbonylpyrrolidin-3-ylmethanol;BP-13175;HY-60218;SY004169;SY020767;SY023073;(3R)-1-Boc-3-(hydroxymethyl)pyrrolidine;1-t-butoxycarbonyl-3-hydroxymethylpyrrolidine;AM20080086;B4249;FT-0647376;FT-0649560;FT-0650091;1-(tert-Butoxycarbonyl)-3-pyrrolidinemethanol;EN300-61991;N-tert-butoxycarbonyl-3-hydroxymethylpyrrolidine;N-tert-butoxycarbonyl-3-(hydroxymethyl)pyrrolidine;t-butyl 3-(hydroxymethyl)-1-pyrrolidinecarboxylate;J-504350;Tert-butyl3-(hydroxymethyl)pyrrolidine-1-carboxylate;1-(tert-butoxycarbonyl)-3-(hydroxymethyl)pyrrolidine;Z976727100;1,1-dimethylethyl 3-(hydroxymethyl)-1-pyrrolidine-carboxylate;1,1-dimethylethyl 3-(hydroxymethyl)-1-pyrrolidinecarboxylate;3-(Hydroxymethyl)pyrrolidine-1-carboxylic Acid tert-Butyl Ester;3-hydroxymethyl-pyrrolidin-1-carboxylic acid tert-butyl ester;3-hydroxyMethylpyrrolidine-1-carboxylic acid tert- butyl ester;3-(hydroxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester;3-Hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester, AldrichCPR;tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

Chemical Property of Tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

Chemical Property:

• Vapor Pressure: 0.000241mmHg at 25°C
• Refractive Index: 1.483
• Boiling Point: 289.5 °C at 760 mmHg
• PKA: 14.93±0.10(Predicted)
• Flash Point: 128.9 °C
• PSA: 49.77000
• Density: 1.084 g/cm³
• LogP: 1.17360
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 201.13649347
• Heavy Atom Count: 14
• Complexity: 210

Purity/Quality:

99% ^*data from raw suppliers

1-Boc-3-hydroxymethylpyrrolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,N,T
• Statements: 25-50
• Safety Statements: 24/25-61-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC(C1)CO
• Uses: 1-Boc-3-hydroxymethylpyrrolidine is an intermediate of SR 9009 (S684255). SR 9009 is a synthetic REV-ERB agonist that regulates circadian behavior and metabolism; has potential use in the treatment of sleep disorders and metabolic diseases.

Technology Process of Tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

There total 17 articles about Tert-butyl 3-(hydroxymethyl)pyrrolidine-1-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: 95.0%

pyrrolidin-3-ylmethanol (85310-69-6,110013-18-8,110013-19-9,5082-74-6) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate (114214-69-6)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 5h; Solvent; Reagent/catalyst; Large scale;

Reference yield: 94.0%

1-t-butyloxycarbonylpyrrole-3-carboxylic acid ethyl ester (170844-49-2,1421256-03-2) → tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate (114214-69-6)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 0 ℃; for 42.5h;

Reference yield: 88.0%

1-boc-pyrrolidine-3-carboxylic acid (72925-16-7,72983-31-4,140148-70-5,59378-75-5) → tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate (114214-69-6)

Guidance literature:

1-boc-pyrrolidine-3-carboxylic acid; With lithium aluminium tetrahydride; In tetrahydrofuran; at -40 - 0 ℃;

With sodium hydroxide; In water; at 20 ℃; for 0.5h;

DOI:10.1016/j.ejmech.2016.12.006

upstream raw materials:

methyl 1-tert-butoxycarbonyl-3-pyrrolidinecarboxylate

pyrrolidin-3-ylmethanol

di-tert-butyl dicarbonate

1-(Phenylmethyl)-3-pyrrolidinemethanol

Downstream raw materials:

3-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

3-iodomethylpyrrolidine-1-carboxylic acid tert-butyl ester

tert-butyl 3-formylpyrrolidine-1-carboxylate

tert-butyl (R)-3-hydroxymethylpyrrolidine-1-carboxylate

Refernces

• 1、 -. "TRPML MODULATORS". Paragraph 0318. . Retrieved 2021/06/26.
• 2、 -. "A process for preparing N - Boc - 3 - pyrrolidine of formaldehyde (by machine translation)". Paragraph 0045; 0048; 0050; 0053. . Retrieved 2019/02/04.