HCID 57554734, compound → HCID 57554684, compound

HRID 1511903Notes

Reaction equation

HRID 1511903 reaction equation
[CH2:1]([O:3][P:4](/[CH:9]=[CH:10]/[C@@:11]1([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:15][CH2:14][C@H:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:18][CH:17]=2)[CH2:12]1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]>C(O)C.[Pd]>[CH2:7]([O:6][P:4]([CH2:9][CH2:10][C@@:11]1([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[CH2:15][CH2:14][C@H:13]([C:16]2[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:20][CH:21]=2)[CH2:12]1)([O:3][CH2:1][CH3:2])=[O:5])[CH3:8]

Participants

4

Reactant 1

HCID 57554734HCID 57554734, compound

Product 1

HCID 57554684HCID 57554684, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Tert-butyl (1R,3S)-1-((E)-2-(diethoxyphosphoryl)vinyl)-3-(4-octylphenyl)cyclopentylcarbamate (0.237 g, 0.442 mmol) was dissolved in ethanol. Palladium on carbon (0.094 g, 0.088 mmol) was added and the reaction was flushed with hydrogen and hydrogenated at atmospheric pressure for about 72 h. The solution was filtered through a syringe filter and washed through with methanol. Solvent was removed under reduced pressure to provide tert-butyl (1R,3S)-1-(2-(diethoxyphosphoryl)ethyl)-3-(4-octylphenyl)cyclopentylcarbamate (0.236 g, 0.439 mmol, 99% yield) as a colorless oil: LC/MS (method f) Rt=3.60 min.; MS m/z: 538.53 (M+H)+.

Workup

  1. customthe reaction was flushed with hydrogen and hydrogenated at atmospheric pressure for about 72 h
  2. filtrationThe solution was filtered through a syringe
  3. filtrationfilter
  4. washwashed through with methanol
  5. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-bb49592ca2854264a955ca45821e04dd
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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