Benzyl ((3R,4R)-4-hydroxy-1-(2-(4-trifluoromethoxyphenyl)ethanoyl)pyrrolidin-3-yl)carbamate → 1-((3R,4R)-3-amino-4-hydroxypyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone

HRID 1666675Notes

Reaction equation

HRID 1666675 reaction equation
[OH:1][C@@H:2]1[CH2:6][N:5]([C:7](=[O:20])[CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)[CH2:4][C@H:3]1[NH:21]C(=O)OCC1C=CC=CC=1>CO.[Pd]>[NH2:21][C@H:3]1[C@H:2]([OH:1])[CH2:6][N:5]([C:7](=[O:20])[CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][C:16]([F:17])([F:18])[F:19])=[CH:13][CH:14]=2)[CH2:4]1

Participants

4

Reactant 1

HCID 57970130Benzyl ((3R,4R)-4-hydroxy-1-(2-(4-trifluoromethoxyphenyl)ethanoyl)pyrrolidin-3-yl)carbamate

Product 1

HCID 579701111-((3R,4R)-3-amino-4-hydroxypyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanoneYield 88.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl ((3R,4R)-4-hydroxy-1-(2-(4-trifluoromethoxyphenyl)ethanoyl)pyrrolidin-3-yl)carbamate (14 g) was dissolved in methanol (140 mL), followed by addition of 5% Pd—C (2.4 g), and the mixture was stirred overnight under hydrogen atmosphere. The catalyst was removed by filtration, and then the filtrate was concentrated under reduced pressure. The precipitated solids were washed with a mixed solvent of isopropyl ether and hexane to obtain the title compound (8.6 g).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washThe precipitated solids were washed with a mixed solvent of isopropyl ether and hexane

Sources & evidence

ORD record
ord-ca3b781f031747beb8a64589fb37a102
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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