methyl (2RS,3RS,5R)-N-(tert-butyloxycarbonyl)-3-hydroxy-5-phenylpyrrolidine-2-carboxylate

Base Information

Chemical Name:methyl (2RS,3RS,5R)-N-(tert-butyloxycarbonyl)-3-hydroxy-5-phenylpyrrolidine-2-carboxylate
CAS No.:434326-87-1
Molecular Formula:C₁₇H₂₃NO₅
Molecular Weight:321.373
Hs Code.:

Synonyms:methyl (2RS,3RS,5R)-N-(tert-butyloxycarbonyl)-3-hydroxy-5-phenylpyrrolidine-2-carboxylate

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Chemical Property of methyl (2RS,3RS,5R)-N-(tert-butyloxycarbonyl)-3-hydroxy-5-phenylpyrrolidine-2-carboxylate

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Technology Process of methyl (2RS,3RS,5R)-N-(tert-butyloxycarbonyl)-3-hydroxy-5-phenylpyrrolidine-2-carboxylate

There total 6 articles about methyl (2RS,3RS,5R)-N-(tert-butyloxycarbonyl)-3-hydroxy-5-phenylpyrrolidine-2-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: 85.0%

: 434326-86-0
methyl (5R)-N-(tert-butyloxycarbonyl)-3-oxo-5-phenylpyrrolidine-2-carboxylate

: 434326-87-1
methyl (2RS,3RS,5R)-N-(tert-butyloxycarbonyl)-3-hydroxy-5-phenylpyrrolidine-2-carboxylate

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h;
DOI:10.1021/ol025831j

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 434326-87-1
methyl (2RS,3RS,5R)-N-(tert-butyloxycarbonyl)-3-hydroxy-5-phenylpyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: TFA / methanol / 2 h / 20 °C

1.2: 84 percent / Et₃N; 4-dimethylaminopyrridine / tetrahydrofuran; methanol / 2 h / 0 °C

2.1: (4-carboxybenzene)sulfonyl azide / acetonitrile / 0 °C

2.2: 98 percent / Et₃N / acetonitrile / 0.5 h

3.1: 0.088 g / Rh₂(OAc)4 / CH₂Cl₂ / 2 h / 20 °C

4.1: 85 percent / NaBH₄ / methanol / 0.5 h / 0 °C

With sodium tetrahydroborate; p-carboxybenzenesulfonyl azide; trifluoroacetic acid; dirhodium tetraacetate; In methanol; dichloromethane; acetonitrile;
DOI:10.1021/ol025831j

Reference yield:

: 267011-72-3
methyl (S_S,R)-(+)-methyl 3-oxo-5-phenyl-5-(p-toluenesulfinylamino)pentanoate

: 434326-87-1
methyl (2RS,3RS,5R)-N-(tert-butyloxycarbonyl)-3-hydroxy-5-phenylpyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: TFA / methanol / 2 h / 20 °C

1.2: 84 percent / Et₃N; 4-dimethylaminopyrridine / tetrahydrofuran; methanol / 2 h / 0 °C

2.1: (4-carboxybenzene)sulfonyl azide / acetonitrile / 0 °C

2.2: 98 percent / Et₃N / acetonitrile / 0.5 h

3.1: 0.088 g / Rh₂(OAc)4 / CH₂Cl₂ / 2 h / 20 °C

4.1: 85 percent / NaBH₄ / methanol / 0.5 h / 0 °C

With sodium tetrahydroborate; p-carboxybenzenesulfonyl azide; trifluoroacetic acid; dirhodium tetraacetate; In methanol; dichloromethane; acetonitrile;
DOI:10.1021/ol025831j