Tert-butyl[(1s,2s)-1-{[(3s)-3-fluoropyrrolidin-1-yl]carbonyl}-2-(4-hydroxyphenyl)propyl]carbamate → Tert-butyl[(1s,2s)-1-{[(3s)-3-fluoropyrrolidin-1-yl]carbonyl}-2-(4-hydroxycyclohexyl)propyl]carbamate

HRID 2242647Notes

Reaction equation

HRID 2242647 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]([C:18]([N:20]1[CH2:24][CH2:23][C@H:22]([F:25])[CH2:21]1)=[O:19])[C@H:9]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[CH3:10])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Rh]>[C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]([C:18]([N:20]1[CH2:24][CH2:23][C@H:22]([F:25])[CH2:21]1)=[O:19])[C@H:9]([CH:11]1[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1)[CH3:10])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 91113754Tert-butyl[(1s,2s)-1-{[(3s)-3-fluoropyrrolidin-1-yl]carbonyl}-2-(4-hydroxyphenyl)propyl]carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 59205303Tert-butyl[(1s,2s)-1-{[(3s)-3-fluoropyrrolidin-1-yl]carbonyl}-2-(4-hydroxycyclohexyl)propyl]carbamate

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

The material from Step B (0.022 g, 0.060 mmol) was hydrogenated at 50 psi hydrogen in the presence of 5% rhodium on alumina (22 mg) in methanol (5 mL) using a Parr shaker. After 24 h, the reaction mixture was filtered by passage through a syringe filter. Concentration of the filtrate in vacuo afforded the title compound as a mixture of cis and trans isomers containing a small amount of the fully reduced cyclohexane. LC/MS 395.3 (M+Na)

Workup

  1. filtrationthe reaction mixture was filtered by passage through a syringe
  2. filtrationfilter

Sources & evidence

ORD record
ord-e8417ccdb93d441eb59dd5792fd0b26d
Source dataset
uspto-grants-2010_03
Patent number
US07671073B2

Reaction notes

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