(3R,4R)-1-[(1R)-1-Phenylethyl]-4-[4-(phenylmethoxy)phenyl]-3-piperidinol hydrochloride → (3R,4R)-4-(4-hydroxy-phenyl)-piperidin-3-ol hydrochloride

HRID 650734Notes

Reaction equation

HRID 650734 reaction equation
[ClH:1].C([O:9][C:10]1[CH:15]=[CH:14][C:13]([C@H:16]2[CH2:21][CH2:20][N:19]([C@@H](C3C=CC=CC=3)C)[CH2:18][C@@H:17]2[OH:30])=[CH:12][CH:11]=1)C1C=CC=CC=1>CO.O.[C].[Pd]>[ClH:1].[OH:9][C:10]1[CH:15]=[CH:14][C:13]([C@H:16]2[CH2:21][CH2:20][NH:19][CH2:18][C@@H:17]2[OH:30])=[CH:12][CH:11]=1

Participants

5

Reactant 1

HCID 69110291(3R,4R)-1-[(1R)-1-Phenylethyl]-4-[4-(phenylmethoxy)phenyl]-3-piperidinol hydrochloride

Product 1

HCID 20677893(3R,4R)-4-(4-hydroxy-phenyl)-piperidin-3-ol hydrochlorideYield 99.6%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The reaction flask was charged under argon with 250 mg of 10% carbon-palladium (Degussa E-101 N/D), then a solution of 5 g (11.8 mmol) of (3R,4R)-4-(4-benzyloxy-phenyl)-1-((R)-1-phenyl-ethyl)-piperidin-3-ol hydrochloride in 50 mL of methanol and 5 mL water was added. After hydogenation during 6 h at room temperature and normal pressure the catalyst was separated by filtration and washed with methanol. The filtrate was concentrated and the remaining water was azeotropically removed at the rotary evaporator using toluene (3×100 mL) to give 2.7 g of (3R,4R)-4-(4-hydroxy-phenyl)-piperidin-3-ol hydrochloride as white crystals.

Workup

  1. customnormal pressure the catalyst was separated by filtration
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated
  4. customthe remaining water was azeotropically removed at the rotary evaporator

Sources & evidence

ORD record
ord-3dc479ccbc7b4d8399cc8c0b0b882dce
Source dataset
uspto-grants-2001_08
Patent number
US06274735B1

Reaction notes

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