Ethanol → (E)-(R)-1-[6-[(R)-2-tert-butoxycarbonyl-pyrrolidin-1-yl)-6-oxo-hex-3-enoyl]-pyrrolidine-2-carboxylic acid tert-butyl ester

HRID 1385772Notes

Reaction equation

HRID 1385772 reaction equation
[C:1]([O:5][C:6](=[O:12])[C@H:7]1[CH2:11][CH2:10][CH2:9][NH:8]1)([CH3:4])([CH3:3])[CH3:2].[C:13]([OH:22])(=O)[CH2:14]/[CH:15]=[CH:16]/[CH2:17][C:18]([OH:20])=O.[CH3:23][CH2:24][OH:25]>CCOC(C)=O>[C:1]([O:5][C:6]([C@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:18](=[O:20])[CH2:17]/[CH:16]=[CH:15]/[CH2:14][C:13]([N:8]1[CH2:7][CH2:11][CH2:10][C@@H:23]1[C:24]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:25])=[O:22])=[O:12])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 5351896trans-beta-Hydromuconic acidHCID 6931635H-D-Pro-otbu

Product 1

HCID 69895037(E)-(R)-1-[6-[(R)-2-tert-butoxycarbonyl-pyrrolidin-1-yl)-6-oxo-hex-3-enoyl]-pyrrolidine-2-carboxylic acid tert-butyl esterYield 77%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using General Procedure A with 1.5 g (8.76 mmol) D-Proline tert-butyl ester and 630 mg (4.37 mmol) trans-3-hexenedioic acid afforded, after flash chromatography (10% EtOH in EtOAc), 1.59 g (77%) of the title compound as a white crystalline solid. MS m/e (%): 568 (M+NH4+, 35), 451 (M+H+, 100), 395 ([M+H−C3H8]+, 32), 339 ([M+H−2C3H8]+, 40).

Workup

  1. customafforded

Sources & evidence

ORD record
ord-e4fc43cea4954525b13614b7e10afcb2
Source dataset
uspto-grants-2001_07
Patent number
US06262089B1

Reaction notes

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