(4S,5R)-4-(benzyloxy)-5-(3-tert-butyldimethylsilyloxypropyl)pyrrolidin-2-one

Base Information

• Chemical Name: (4S,5R)-4-(benzyloxy)-5-(3-tert-butyldimethylsilyloxypropyl)pyrrolidin-2-one
• CAS No.: 1268602-44-3
• Molecular Formula: C₂₀H₃₃NO₃Si
• Molecular Weight: 363.572
• Mol file: 1268602-44-3.mol

Synonyms:(4S,5R)-4-(benzyloxy)-5-(3-tert-butyldimethylsilyloxypropyl)pyrrolidin-2-one

Chemical Property of (4S,5R)-4-(benzyloxy)-5-(3-tert-butyldimethylsilyloxypropyl)pyrrolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-4-(benzyloxy)-5-(3-tert-butyldimethylsilyloxypropyl)pyrrolidin-2-one

There total 4 articles about (4S,5R)-4-(benzyloxy)-5-(3-tert-butyldimethylsilyloxypropyl)pyrrolidin-2-one 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: 85.0%

(4S,5R)-4-(benzyloxy)-5-(3-hydroxypropyl)pyrrolidin-2-one (1268602-43-2) + tert-butyldimethylsilyl chloride (18162-48-6) → (4S,5R)-4-(benzyloxy)-5-(3-tert-butyldimethylsilyloxypropyl)pyrrolidin-2-one (1268602-44-3)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1039/c0cc04371k

Reference yield:

(S)-1-allyl-3-(benzyloxy)pyrrolidine-2,5-dione (1185870-84-1) → (4S,5R)-4-(benzyloxy)-5-(3-tert-butyldimethylsilyloxypropyl)pyrrolidin-2-one (1268602-44-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: magnesium / tetrahydrofuran

1.2: 8 h / 0 °C

2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / -55 - 20 °C

3.1: rhodium(III) trichloride hydrate / ethanol / 6 h / Reflux

3.2: 48 h / Reflux

3.3: 24 h / 0 - 20 °C / Reflux; Inert atmosphere

4.1: 1H-imidazole; dmap / dichloromethane / 24 h / 20 °C / Inert atmosphere

With 1H-imidazole; triethylsilane; dmap; rhodium(III) trichloride hydrate; boron trifluoride diethyl etherate; magnesium; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1039/c0cc04371k

Reference yield:

(4S,5R)-1-allyl-4-(benzyloxy)-5-(3-hydroxypropyl)pyrrolidin-2-one (1268602-42-1) → (4S,5R)-4-(benzyloxy)-5-(3-tert-butyldimethylsilyloxypropyl)pyrrolidin-2-one (1268602-44-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: rhodium(III) trichloride hydrate / ethanol / 6 h / Reflux

1.2: 48 h / Reflux

1.3: 24 h / 0 - 20 °C / Reflux; Inert atmosphere

2.1: 1H-imidazole; dmap / dichloromethane / 24 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; rhodium(III) trichloride hydrate; In ethanol; dichloromethane;

DOI:10.1039/c0cc04371k

upstream raw materials:

(S)-1-allyl-3-(benzyloxy)pyrrolidine-2,5-dione

(4S,5R)-1-allyl-4-(benzyloxy)-5-(3-hydroxypropyl)pyrrolidin-2-one

C₂₃H₃₇NO₄Si

(4S,5R)-4-(benzyloxy)-5-(3-hydroxypropyl)pyrrolidin-2-one

Downstream raw materials:

tert-butyl (2R,3S)-3-(benzyloxy)-2-(3-tert-butyldimethylsilyloxypropyl)-5-oxopyrrolidine-1-carboxylate