Ethyl Acetate → HCID 46214533, compound

HRID 880722Notes

Reaction equation

HRID 880722 reaction equation
C(OCC)(=O)C.C(OC(=O)[NH:16][C@H:17]([CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[C:18]([N:20]1[CH2:25][CH2:24][CH:23]([C:26]2[CH:31]=[CH:30][C:29]([O:32]CC3C=CC=CC=3)=[CH:28][C:27]=2[O:40]CC2C=CC=CC=2)[CH2:22][CH2:21]1)=[O:19])C1C=CC=CC=1>CO.[Pd]>[NH2:16][C@H:17]([CH2:48][C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)[C:18]([N:20]1[CH2:25][CH2:24][CH:23]([C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][C:27]=2[OH:40])[CH2:22][CH2:21]1)=[O:19]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 70921766HCID 70921766, compound

Product 1

HCID 46214533HCID 46214533, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

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 15 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-c9bd69d2cf79443ba232482f76d6ec26
Source dataset
uspto-grants-2015_03
Patent number
US08993596B2

Reaction notes

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