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

Base Information

• Chemical Name: (2S,5S)-1-[(Benzyloxy)carbonyl]-2-tosyloxymethyl-5-(pent-4-enyl)pyrrolidine
• CAS No.: 158149-93-0
• Molecular Formula: C₂₅H₃₁NO₅S
• Molecular Weight: 457.591
• Mol file: 158149-93-0.mol

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

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

There total 10 articles about (2S,5S)-1-[(Benzyloxy)carbonyl]-2-tosyloxymethyl-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: 96.0%

p-toluenesulfonyl chloride (98-59-9) + (2S,5S)-1-[(Benzyloxy)carbonyl]-2-hydroxymethyl-5-(pent-4-enyl)pyrrolidine (158149-94-1) → (2S,5S)-1-[(Benzyloxy)carbonyl]-2-tosyloxymethyl-5-(pent-4-enyl)pyrrolidine (158149-93-0) + (2S,5R)-5-(4-pentenyl)-tetrahydro-pyrrolo[1,2-c]oxazol-3-one

Guidance literature:

With triethylamine; at 20 ℃; for 3h;

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

Reference yield:

(5S)-2-Methoxy-1-[(benzyloxy)carbonyl]-5-methoxycarbonylpyrrolidine (214072-10-3) → (2S,5S)-1-[(Benzyloxy)carbonyl]-2-tosyloxymethyl-5-(pent-4-enyl)pyrrolidine (158149-93-0)

Guidance literature:

Multi-step reaction with 3 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

3: 96 percent / Et₃N / 3 h / 20 °C

With sodium tetrahydroborate; copper(I) bromide dimethylsulfide complex; triethylamine; calcium chloride; boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; ethanol; 1: Substitution / 2: Reduction / 3: Tosylation;

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

Reference yield:

N-carbobenzyloxy-L-proline methyl ester (5211-23-4) → (2S,5S)-1-[(Benzyloxy)carbonyl]-2-tosyloxymethyl-5-(pent-4-enyl)pyrrolidine (158149-93-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / tetraethylammonium p-toluenesulfonate / -5 °C / Electrolysis; GC-monitoring

2: 79.5 percent / CuBr_.DMS / BF_3.Et₂O / diethyl ether / -78 °C / heating to 20 deg C during 4-5 h

3: 73.6 percent / NaBH₄; CaCl₂ / ethanol; tetrahydrofuran / 18 h / -5 °C

4: 96 percent / Et₃N / 3 h / 20 °C

With sodium tetrahydroborate; copper(I) bromide dimethylsulfide complex; tetraethylammonium tosylate; triethylamine; calcium chloride; boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; ethanol; 1: Methoxylation / 2: Substitution / 3: Reduction / 4: Tosylation;

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

upstream raw materials:

p-toluenesulfonyl chloride

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

4-penten-1-yllithium

N-carbobenzyloxy-L-proline methyl ester

Downstream raw materials:

(-)-indolizidine 223AB

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

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

(2R,5R)-N-<(benzyloxy)carbonyl>-2-(4-hydroxyheptyl)-5-butylpyrrolidine