HCID 22382441, compound → HCID 58860068, compound

HRID 895881Notes

Reaction equation

HRID 895881 reaction equation
CC(C)([O-])C.[K+].[CH:7]1([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])=[O:11])[CH2:9][CH2:8]1>C(O)(C)C>[CH:7]1([C@H:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:21])[CH3:22])[OH:11])[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 22382441HCID 22382441, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 58860068HCID 58860068, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of dichloro[(S)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl][(S)-1,1′-bis(p-methoxyphenyl)-2-isopropylethane-1,2-diamine]ruthenium (II) (111 mg) and potassium-tert-butoxide (44.9 mg) in isopropanol (100 ml) was added (cyclopropyl)[2-(tert-butyldimethylsilyloxymethyl)phenyl]methanone (5.81 g) obtained in Step 2, and the mixture was subjected to medium pressure hydrogenation (5.0 kgf/cm2) at room temperature for 36 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5) to give the title compound (5.82 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-3744d5130ee74c5fbf83450faafe7840
Source dataset
uspto-grants-2005_07
Patent number
US06916956B2

Reaction notes

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