tert-butyl (2R)-1-[(benzyloxy)carbonyl]-2-{[(2S,4R)-4-hydroxy-2-(methoxycarbonyl)pyrrolidin-1-yl]carbonyl}pyrrolidine-2-acetate

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Chemical Name:tert-butyl (2R)-1-[(benzyloxy)carbonyl]-2-{[(2S,4R)-4-hydroxy-2-(methoxycarbonyl)pyrrolidin-1-yl]carbonyl}pyrrolidine-2-acetate
CAS No.:195453-64-6
Molecular Formula:C₂₅H₃₄N₂O₈
Molecular Weight:490.554
Hs Code.:

Synonyms:tert-butyl (2R)-1-[(benzyloxy)carbonyl]-2-{[(2S,4R)-4-hydroxy-2-(methoxycarbonyl)pyrrolidin-1-yl]carbonyl}pyrrolidine-2-acetate

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Chemical Property of tert-butyl (2R)-1-[(benzyloxy)carbonyl]-2-{[(2S,4R)-4-hydroxy-2-(methoxycarbonyl)pyrrolidin-1-yl]carbonyl}pyrrolidine-2-acetate

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Technology Process of tert-butyl (2R)-1-[(benzyloxy)carbonyl]-2-{[(2S,4R)-4-hydroxy-2-(methoxycarbonyl)pyrrolidin-1-yl]carbonyl}pyrrolidine-2-acetate

There total 4 articles about tert-butyl (2R)-1-[(benzyloxy)carbonyl]-2-{[(2S,4R)-4-hydroxy-2-(methoxycarbonyl)pyrrolidin-1-yl]carbonyl}pyrrolidine-2-acetate 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: 42.0%

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 195453-61-3
2-tert-Butoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

: 195453-64-6
tert-butyl (2R)-1-[(benzyloxy)carbonyl]-2-{[(2S,4R)-4-hydroxy-2-(methoxycarbonyl)pyrrolidin-1-yl]carbonyl}pyrrolidine-2-acetate

: 195453-67-9
tert-butyl (2S)-1-[(benzyloxy)carbonyl]-2-{[(2S,4R)-4-hydroxy-2-(methoxycarbonyl)pyrrolidin-1-yl]carbonyl}pyrrolidine-2-acetate

Guidance literature:: With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 4.5h; Ambient temperature;
DOI:10.1002/hlca.19970800514

Reference yield:

: 5211-23-4
N-carbobenzyloxy-L-proline methyl ester

: 195453-64-6
tert-butyl (2R)-1-[(benzyloxy)carbonyl]-2-{[(2S,4R)-4-hydroxy-2-(methoxycarbonyl)pyrrolidin-1-yl]carbonyl}pyrrolidine-2-acetate

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / LDA/THF complex / tetrahydrofuran; hexane

2: 83 percent / LiOH*H₂O / methanol; H₂O / 15 h

3: 45 percent / i-Pr₂EtN, O-(1H-benzotriazol-1-yl)-N,N,N'',N''-tetramethyluronium hexafluorophosphate / CH₂Cl₂ / 4.5 h / Ambient temperature

With tetrahydrofuran; lithium hydroxide; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; water;
DOI:10.1002/hlca.19970800514

Reference yield:

: 195453-57-7
2-tert-Butoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 195453-64-6
tert-butyl (2R)-1-[(benzyloxy)carbonyl]-2-{[(2S,4R)-4-hydroxy-2-(methoxycarbonyl)pyrrolidin-1-yl]carbonyl}pyrrolidine-2-acetate

Guidance literature:: Multi-step reaction with 2 steps

1: 83 percent / LiOH*H₂O / methanol; H₂O / 15 h

2: 45 percent / i-Pr₂EtN, O-(1H-benzotriazol-1-yl)-N,N,N'',N''-tetramethyluronium hexafluorophosphate / CH₂Cl₂ / 4.5 h / Ambient temperature

With lithium hydroxide; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; water;
DOI:10.1002/hlca.19970800514