HCID 70921766, compound → HCID 46214533, compound

HRID 2365918Notes

Reaction equation

HRID 2365918 reaction equation
C(OC(=O)[NH:10][C@H:11]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:12]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26]CC3C=CC=CC=3)=[CH:22][C:21]=2[O:34]CC2C=CC=CC=2)[CH2:16][CH2:15]1)=[O:13])C1C=CC=CC=1>CO.C(OCC)(=O)C.[Pd]>[NH2:10][C@H:11]([CH2:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[C:12]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][C:21]=2[OH:34])[CH2:16][CH2:15]1)=[O:13]

Participants

5

Reactant 1

HCID 70921766HCID 70921766, compound

Product 1

HCID 46214533HCID 46214533, compoundYield 97.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 25 ml round-bottomed flask, 1.23 g of {(R)-1-benzyl-2-[4-(2,4-bis(benzyloxy)phenyl)piperidin-1-yl]-2-oxoethyl}carbamic acid benzyl ester are dissolved in ml of methanol and also 15 ml of ethyl acetate in the presence of 0.25 g of palladium-on-charcoal at 10%. The reaction mixture is stirred for 18 hours under a hydrogen atmosphere. The reaction mixture is filtered. The residue is chromatographed on silica gel (95/5 dichloromethane/methanol). 0.625 g of (R)-2-amino-1-[4-(2,4-dihydroxyphenyl)piperidin-1-yl]-3-phenylpropan-1-one is obtained. Yield=64%.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customThe residue is chromatographed on silica gel (95/5 dichloromethane/methanol)

Sources & evidence

ORD record
ord-c3916e8425e8431989e39aa02720246f
Source dataset
uspto-grants-2014_04
Patent number
US08697726B2

Reaction notes

Loading…