HCID 22382441, compound → HCID 58860075, compound

HRID 1349456Notes

Reaction equation

HRID 1349456 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 58860075HCID 58860075, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of dichloro[(R)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl][(R)-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 of Example 58, 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 (5.50 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-2cae7b28a86545d19b67eb096153ad7d
Source dataset
uspto-grants-2007_05
Patent number
US07211685B2

Reaction notes

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