(1S,2S)-1,2-diphenylethane-1,2-diamine → (R)-(Cyclopropyl)(2-methylphenyl)methanol

HRID 895878

Reaction equation

HRID 895878 reaction equation
C1([C@H](N)[C@H](C2C=CC=CC=2)N)C=CC=CC=1.CC(C)([O-])C.[K+].[CH3:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]([CH:32]1[CH2:34][CH2:33]1)=[O:31]>C(O)(C)C>[CH:32]1([C@H:30]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[CH3:23])[OH:31])[CH2:33][CH2:34]1

Participants

5

Reactant 3

HCID 6931238(1S,2S)-1,2-diphenylethane-1,2-diamineHCID 22382440Cyclopropyl(2-methylphenyl)methanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 60017546(R)-(Cyclopropyl)(2-methylphenyl)methanolYield 71.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of dichloro[(S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl]ruthenium(II) (851 mg), (1S,2S)-(−)-1,2-diphenylethylenediamine (191 mg) and potassium-tert-butoxide (270 mg) in isopropanol (90 ml) was added cyclopropyl 2-methylphenyl ketone (9.61 g) obtained in Step 2, and the mixture was hydrogenated at room temperature and at medium pressure (3.0 kgf/cm2) for 60 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9) to give the title compound (6.92 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9)

Sources & evidence

ORD record
ord-74798a6b2b8a4d54a84e2a74d5137c20
Source dataset
uspto-grants-2005_07
Patent number
US06916956B2

Linked notes

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