(3S,4S,1'S)-4-benzoyloxymethyl-3-t-butyldimethylsilyloxy-1-(1'-phenylethyl)pyrrolidin-2-one

Base Information

• Chemical Name: (3S,4S,1'S)-4-benzoyloxymethyl-3-t-butyldimethylsilyloxy-1-(1'-phenylethyl)pyrrolidin-2-one
• CAS No.: 859214-21-4
• Molecular Formula: C₂₆H₃₅NO₄Si
• Molecular Weight: 453.654

Synonyms:(3S,4S,1'S)-4-benzoyloxymethyl-3-t-butyldimethylsilyloxy-1-(1'-phenylethyl)pyrrolidin-2-one

Chemical Property of (3S,4S,1'S)-4-benzoyloxymethyl-3-t-butyldimethylsilyloxy-1-(1'-phenylethyl)pyrrolidin-2-one

Chemical Property:

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Technology Process of (3S,4S,1'S)-4-benzoyloxymethyl-3-t-butyldimethylsilyloxy-1-(1'-phenylethyl)pyrrolidin-2-one

There total 2 articles about (3S,4S,1'S)-4-benzoyloxymethyl-3-t-butyldimethylsilyloxy-1-(1'-phenylethyl)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:

(3S,4S,1'S)-3-tert-butyldimethylsilyloxy-4-methoxycarbonyl-1-(1'-phenylethyl)pyrrolidin-2-one (807626-26-2) → (3S,4S,1'S)-4-benzoyloxymethyl-3-t-butyldimethylsilyloxy-1-(1'-phenylethyl)pyrrolidin-2-one (859214-21-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium borohydride; sodium ethoxide / ethanol / 6 h / 20 °C

2: 2.0 g / triethylamine / CH₂Cl₂ / 4 h / cooling

With sodium tetrahydroborate; sodium ethanolate; triethylamine; In ethanol; dichloromethane;

DOI:10.1016/j.tetasy.2005.03.003

Reference yield:

benzoyl chloride (98-88-4) + (3S,4S,1'S)-3-tert-butyldimethylsilyloxy-4-hydroxymethyl-1-(1'-phenylethyl)pyrrolidin-2-one (807626-37-5) → (3S,4S,1'S)-4-benzoyloxymethyl-3-t-butyldimethylsilyloxy-1-(1'-phenylethyl)pyrrolidin-2-one (859214-21-4)

Guidance literature:

With triethylamine; In dichloromethane; for 4h; cooling;

DOI:10.1016/j.tetasy.2005.03.003

Reference yield: 76.0%

(3S,4S,1'S)-4-benzoyloxymethyl-3-t-butyldimethylsilyloxy-1-(1'-phenylethyl)pyrrolidin-2-one (859214-21-4) → (3S,4S,1'S)-4-benzoyloxymethyl-3-hydroxy-1-(1'-phenylethyl)pyrrolidin-2-one (859214-22-5)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 2h;

DOI:10.1016/j.tetasy.2005.03.003

upstream raw materials:

benzoyl chloride

(3S,4S,1'S)-3-tert-butyldimethylsilyloxy-4-hydroxymethyl-1-(1'-phenylethyl)pyrrolidin-2-one

(3S,4S,1'S)-3-tert-butyldimethylsilyloxy-4-methoxycarbonyl-1-(1'-phenylethyl)pyrrolidin-2-one

Downstream raw materials:

(3S,4S,1'S)-4-benzoyloxymethyl-3-hydroxy-1-(1'-phenylethyl)pyrrolidin-2-one

(3S,4S,1'S)-4-benzoyloxymethyl-3-methanesulfonyloxy-1-(1'-phenylethyl)pyrrolidin-2-one

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