(2S)-(-)-phenylmethyl 2-(1,2-dihydroxyethyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: (2S)-(-)-phenylmethyl 2-(1,2-dihydroxyethyl)pyrrolidine-1-carboxylate
• CAS No.: 623938-26-1
• Molecular Formula: C₁₄H₁₉NO₄
• Molecular Weight: 265.309
• Mol file: 623938-26-1.mol

Synonyms:(2S)-(-)-phenylmethyl 2-(1,2-dihydroxyethyl)pyrrolidine-1-carboxylate

Chemical Property of (2S)-(-)-phenylmethyl 2-(1,2-dihydroxyethyl)pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (2S)-(-)-phenylmethyl 2-(1,2-dihydroxyethyl)pyrrolidine-1-carboxylate

There total 3 articles about (2S)-(-)-phenylmethyl 2-(1,2-dihydroxyethyl)pyrrolidine-1-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: 97.0%

C16H19NO5 → (2S)-(-)-phenylmethyl 2-(1,2-dihydroxyethyl)pyrrolidine-1-carboxylate (623938-26-1)

Guidance literature:

C₁₆H₁₉NO₅; With sodium tetrahydroborate; In tetrahydrofuran; at -10 - 20 ℃; for 3h;

With sodium methylate; In methanol; at -10 ℃; for 1h;

DOI:10.1016/j.ejmech.2016.10.048

Reference yield: 72.0%

(2S)-(-)-phenylmethyl 2-vinylpyrrolidine-1-carboxylate (141521-11-1) → (2S)-(-)-phenylmethyl 2-(1,2-dihydroxyethyl)pyrrolidine-1-carboxylate (623938-26-1)

Guidance literature:

With tert.-butylhydroperoxide; osmium(VIII) oxide; tetraethylammonium acetate; In acetone; tert-butyl alcohol; at 0 - 20 ℃; for 11h;

DOI:10.1016/S0968-0896(03)00236-0

Reference yield:

2-(S)-(2-bromo-1-oxoethyl)pyrrolidine-1-carboxylic acid benzyl ester (223785-66-8) → (2S)-(-)-phenylmethyl 2-(1,2-dihydroxyethyl)pyrrolidine-1-carboxylate (623938-26-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetone / 2 h / 20 °C

2.1: sodium tetrahydroborate / tetrahydrofuran / 3 h / -10 - 20 °C

2.2: 1 h / -10 °C

With sodium tetrahydroborate; In tetrahydrofuran; acetone;

DOI:10.1016/j.ejmech.2016.10.048

upstream raw materials:

(2S)-(-)-phenylmethyl 2-vinylpyrrolidine-1-carboxylate

2-(S)-(2-bromo-1-oxoethyl)pyrrolidine-1-carboxylic acid benzyl ester

Downstream raw materials:

(2S)-phenylmethyl 2-(2-methyl-1,3-dioxolan-4-yl)pyrrolidine-1-carboxylate