Methyl (2R,5S)-1-benzyl-5-(hydroxymethyl)pyrrolidine-2-carboxylate

Base Information

Chemical Name:Methyl (2R,5S)-1-benzyl-5-(hydroxymethyl)pyrrolidine-2-carboxylate
CAS No.:113304-86-2
Molecular Formula:C₁₄H₁₉NO₃
Molecular Weight:249.31
Hs Code.:
DSSTox Substance ID:DTXSID001164166
Nikkaji Number:J2.954.806D
Mol file:113304-86-2.mol

Synonyms:Methyl (2R,5S)-1-benzyl-5-(hydroxymethyl)pyrrolidine-2-carboxylate;113304-86-2;starbld0038657;DTXSID001164166;D-Proline, 5-(hydroxymethyl)-1-(phenylmethyl)-, methyl ester, cis-;1-Benzyl-5beta-(hydroxymethyl)pyrrolidine-2beta-carboxylic acid methyl ester

Suppliers and Price of Methyl (2R,5S)-1-benzyl-5-(hydroxymethyl)pyrrolidine-2-carboxylate

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
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Total 3 raw suppliers

Chemical Property of Methyl (2R,5S)-1-benzyl-5-(hydroxymethyl)pyrrolidine-2-carboxylate

Chemical Property:

XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:249.13649347
Heavy Atom Count:18
Complexity:276

Purity/Quality:: 99% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:COC(=O)C1CCC(N1CC2=CC=CC=C2)CO
Isomeric SMILES:COC(=O)[C@H]1CC[C@H](N1CC2=CC=CC=C2)CO

Technology Process of Methyl (2R,5S)-1-benzyl-5-(hydroxymethyl)pyrrolidine-2-carboxylate

There total 1 articles about Methyl (2R,5S)-1-benzyl-5-(hydroxymethyl)pyrrolidine-2-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:

: 102572-59-8
(2S,5R)-N-benzyl-5-methoxycarbonylproline

: 113304-86-2
(2R,5S)-1-Benzyl-5-hydroxymethyl-pyrrolidine-2-carboxylic acid methyl ester

Guidance literature:: With sodium tetrahydroborate; chloroformic acid ethyl ester; triethylamine; Yield given. Multistep reaction; 1.) THF, 0 deg C, 3 h, 2.) H₂O, 0 deg C, 1 h;
DOI:10.1021/jo951469t

Reference yield:

: 113304-86-2
(2R,5S)-1-Benzyl-5-hydroxymethyl-pyrrolidine-2-carboxylic acid methyl ester

: 172885-66-4
(2S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 2.40 g / imidazole / dimethylformamide / 24 h / 25 °C

2: DIBALH / toluene; hexane / 0.83 h / 25 °C

3: 100 percent / H₂ / Pd(OH)2/C / ethanol / 18 h / 25 °C / 760 Torr

4: 93 percent / Et₃N / CH₂Cl₂ / 18 h / 0 °C

With 1H-imidazole; hydrogen; diisobutylaluminium hydride; triethylamine; palladium dihydroxide; In ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo951469t

Reference yield:

: 113304-86-2
(2R,5S)-1-Benzyl-5-hydroxymethyl-pyrrolidine-2-carboxylic acid methyl ester

: (2S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-[(dimethoxy-phosphoryl)-hydroxy-methyl]-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 2.40 g / imidazole / dimethylformamide / 24 h / 25 °C

2: DIBALH / toluene; hexane / 0.83 h / 25 °C

3: 100 percent / H₂ / Pd(OH)2/C / ethanol / 18 h / 25 °C / 760 Torr

4: 93 percent / Et₃N / CH₂Cl₂ / 18 h / 0 °C

5: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) -78 deg C, 5 min; -78 deg C -> room temperature

6: 1.) NaH / 1.) DMF, 1 h, 2.) 0 deg C, 48 h

With 1H-imidazole; oxalyl dichloride; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo951469t