3-[(1S,2R)-2-(Benzyloxy)cyclopentyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole → (1R,2S)-2-[1-(Tetrahydro-2H-pyran-2-yl)-1H-pyrazol-3-yl]cyclopentanol

HRID 337977Notes

Reaction equation

HRID 337977 reaction equation
C([O:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]1[CH:18]=[CH:17][N:16]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[N:15]=1)C1C=CC=CC=1>[C].[Pd].C(O)C>[O:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH:19]1[N:16]1[CH:17]=[CH:18][C:14]([C@@H:10]2[CH2:11][CH2:12][CH2:13][C@H:9]2[OH:8])=[N:15]1

Participants

4

Reactant 1

HCID 899619363-[(1S,2R)-2-(Benzyloxy)cyclopentyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole

Product 1

HCID 89962897(1R,2S)-2-[1-(Tetrahydro-2H-pyran-2-yl)-1H-pyrazol-3-yl]cyclopentanolYield 89%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 106b by using the 3-[(1S,2R)-2-(benzyloxy)cyclopentyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol (419 mg, 1.28 mmol) prepared in Example 149b, palladium carbon (5%; 400 mg) and ethanol (20 mL), to yield the title compound (269 mg, 89%) in the form of a diastereomeric mixture as a colorless oil.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-9f99b2883f3c4fa6b11a4a012d1d6b2a
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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