(S)-4-{2-[2-hydroxy-3-(4-benzyloxyphenoxy)propylamino]ethyl}phenoxymethylcyclohexylphosphinic acid, n-butyl ester → (S)-4-{2-[2-Hydroxy-3-(4-hydroxyphenoxy)propylamino]ethyl}phenoxymethylcyclohexylphosphinic acid, n-butyl ester

HRID 1548Notes

Reaction equation

HRID 1548 reaction equation
[OH:1][CH:2]([CH2:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([O:36]CC2C=CC=CC=2)=[CH:32][CH:31]=1)[CH2:3][NH:4][CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH:10]([P@:13]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:19])[O:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:9][CH2:8]1>CO.[Pd]>[OH:1][CH:2]([CH2:28][O:29][C:30]1[CH:31]=[CH:32][C:33]([OH:36])=[CH:34][CH:35]=1)[CH2:3][NH:4][CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH:10]([P@:13]([CH2:20][O:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)(=[O:19])[O:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:9][CH2:8]1

Participants

4

Reactant 1

HCID 86752197(S)-4-{2-[2-hydroxy-3-(4-benzyloxyphenoxy)propylamino]ethyl}phenoxymethylcyclohexylphosphinic acid, n-butyl ester

Product 1

HCID 86752204(S)-4-{2-[2-Hydroxy-3-(4-hydroxyphenoxy)propylamino]ethyl}phenoxymethylcyclohexylphosphinic acid, n-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (S)-4-{2-[2-hydroxy-3-(4-benzyloxyphenoxy)propylamino]ethyl}phenoxymethylcyclohexylphosphinic acid, n-butyl ester (1.00 g, 1.64 mMol) in methanol (100 ml) containing 10% palladium on charcoal (50 mg) was hydrogenated at 40° C. and 40 p.s.i. for 24 hours. After cooling to room temperature the suspension was filtered through a pad of filter aid and the filtrate was evaporated giving the title compound.

Workup

  1. customwas hydrogenated at 40° C.
  2. filtrationwas filtered through a pad of filter aid
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-722dbda67fac4d1c8121beafd45c9dbf
Source dataset
uspto-grants-1998_03
Patent number
US05726165

Reaction notes

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