Benzyl [4-(3-hydroxy-1-methylpiperidin-4-yl)-2-(propan-2-yloxy)phenyl]carbamate → 4-(4-Amino-3-isopropoxyphenyl)-1-methylpiperidin-3-OL

HRID 518808Notes

Reaction equation

HRID 518808 reaction equation
[OH:1][CH:2]1[CH:7]([C:8]2[CH:13]=[CH:12][C:11]([NH:14]C(=O)OCC3C=CC=CC=3)=[C:10]([O:25][CH:26]([CH3:28])[CH3:27])[CH:9]=2)[CH2:6][CH2:5][N:4]([CH3:29])[CH2:3]1>CO>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([CH:7]2[CH2:6][CH2:5][N:4]([CH3:29])[CH2:3][CH:2]2[OH:1])=[CH:9][C:10]=1[O:25][CH:26]([CH3:28])[CH3:27]

Participants

3

Reactant 1

HCID 86697979Benzyl [4-(3-hydroxy-1-methylpiperidin-4-yl)-2-(propan-2-yloxy)phenyl]carbamate

Product 1

HCID 866979804-(4-Amino-3-isopropoxyphenyl)-1-methylpiperidin-3-OLYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

178 mg of benzyl [4-(3-hydroxy-1-methylpiperidin-4-yl)-2-(propan-2-yloxy)phenyl]carbamate (mixture of the cis diastereoisomers) are dissolved in 45 ml of methanol. The solution is filtered on 0.45 μm Acrodisc and then hydrogenated in an H-cube (Pd/C 10% cartridge and P H2=1 atm). The reaction medium is evaporated to dryness under reduced pressure, so as to give 111 mg of 4-[4-amino-3-(propan-2-yloxy)phenyl]-1-methylpiperidin-3-ol in the form of an orangey-coloured solid (mixture of the cis diastereoisomers).

Workup

  1. filtrationThe solution is filtered on 0.45 μm Acrodisc
  2. customThe reaction medium is evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-216e73e9b9b7466996de058a7ea10220
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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