(2S,5S)-1-[(Benzyloxy)carbonyl]-2-hydroxymethyl-5-(pent-4-enyl)pyrrolidine

Base Information

• Chemical Name: (2S,5S)-1-[(Benzyloxy)carbonyl]-2-hydroxymethyl-5-(pent-4-enyl)pyrrolidine
• CAS No.: 158149-94-1
• Molecular Formula: C₁₈H₂₅NO₃
• Molecular Weight: 303.401
• Mol file: 158149-94-1.mol

Synonyms:(2S,5S)-1-[(Benzyloxy)carbonyl]-2-hydroxymethyl-5-(pent-4-enyl)pyrrolidine

Chemical Property of (2S,5S)-1-[(Benzyloxy)carbonyl]-2-hydroxymethyl-5-(pent-4-enyl)pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S)-1-[(Benzyloxy)carbonyl]-2-hydroxymethyl-5-(pent-4-enyl)pyrrolidine

There total 10 articles about (2S,5S)-1-[(Benzyloxy)carbonyl]-2-hydroxymethyl-5-(pent-4-enyl)pyrrolidine 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: 73.6%

(2S,5R)-1-[(Benzyloxy)carbonyl]-2-methoxycarbonyl-5-(pent-4-enyl)pyrrolidine (158149-95-2) → (2S,5S)-1-[(Benzyloxy)carbonyl]-2-hydroxymethyl-5-(pent-4-enyl)pyrrolidine (158149-94-1) + (2S,5R)-5-(4-pentenyl)-tetrahydro-pyrrolo[1,2-c]oxazol-3-one

Guidance literature:

With sodium tetrahydroborate; calcium chloride; In tetrahydrofuran; ethanol; at -5 ℃; for 18h;

DOI:10.1016/S0040-4020(98)00498-0

Reference yield: 67.0%

(S)-5-Pent-4-enyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester → (2S,5S)-1-[(Benzyloxy)carbonyl]-2-hydroxymethyl-5-(pent-4-enyl)pyrrolidine (158149-94-1)

Guidance literature:

With sodium tetrahydroborate; calcium chloride; In tetrahydrofuran; ethanol;

DOI:10.1016/0957-4166(96)00187-5

Reference yield:

(5S)-2-Methoxy-1-[(benzyloxy)carbonyl]-5-methoxycarbonylpyrrolidine (214072-10-3) → (2S,5S)-1-[(Benzyloxy)carbonyl]-2-hydroxymethyl-5-(pent-4-enyl)pyrrolidine (158149-94-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 79.5 percent / CuBr_.DMS / BF_3.Et₂O / diethyl ether / -78 °C / heating to 20 deg C during 4-5 h

2: 73.6 percent / NaBH₄; CaCl₂ / ethanol; tetrahydrofuran / 18 h / -5 °C

With sodium tetrahydroborate; copper(I) bromide dimethylsulfide complex; calcium chloride; boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; ethanol; 1: Substitution / 2: Reduction;

DOI:10.1016/S0040-4020(98)00498-0

upstream raw materials:

(2S,5R)-1-[(Benzyloxy)carbonyl]-2-methoxycarbonyl-5-(pent-4-enyl)pyrrolidine

4-penten-1-yllithium

N-carbobenzyloxy-L-proline methyl ester

(5S)-2-Methoxy-1-[(benzyloxy)carbonyl]-5-methoxycarbonylpyrrolidine

Downstream raw materials:

(2S,5S)-1-[(Benzyloxy)carbonyl]-2-tosyloxymethyl-5-(pent-4-enyl)pyrrolidine

(-)-indolizidine 223AB

(3R,5S,8aR)-3-butyl-5-propyloctahydroindolidine

(2R,5R)-N-<(benzyloxy)carbonyl>-5-butyl-2-(4-oxopentyl)pyrrolidine