(1R)-3-chloro-1-phenylpropan-1-ol → HCID 11788595, compound

HRID 1936189Notes

Reaction equation

HRID 1936189 reaction equation
[Cl:1][CH2:2][CH2:3][C@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5]>CO.[Rh]>[Cl:1][CH2:2][CH2:3][C@H:4]([CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[OH:5]

Participants

4

Reactant 1

HCID 642409(1R)-3-chloro-1-phenylpropan-1-ol

Product 1

HCID 11788595HCID 11788595, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4.25 g (25 mmol) of (R)-3-chloro-1-phenyl-1-propanol in 20 mL of methanol, containing 0.75 g of 5% rhodium-on-alumina, was hydrogenated at 60-65 psig at RT on a Parr shaker for 6.5 hours. The solution was filtered and concentrated, and the crude product was purified by chromatography on silica to give 2.32 g (55%) of (R)-3-chloro-1-cyclohexyl-1-propanol. NMR (DMSO-d6) δ0.8-1.3 (m, 5H), 1.5-1.9 (m, 6H), 3.30 (m, 1H), 3.68 (2 overlapping t, J=5.2 and 7.0, 2H), 4.48 (d, J=5.9, 1H, exchanges).

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated
  3. customthe crude product was purified by chromatography on silica

Sources & evidence

ORD record
ord-5bdfc70a257240c08734880e7bbc464c
Source dataset
uspto-grants-2002_05
Patent number
US06388128B1

Reaction notes

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