3,4-dihydro-2H-pyran → 3-[(1S,2R)-2-(Benzyloxy)cyclopentyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole

HRID 337976Notes

Reaction equation

HRID 337976 reaction equation
[CH2:1]([O:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]1[NH:18][N:17]=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:19]1[CH:24]=[CH:23][CH2:22][CH2:21][CH2:20]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[CH2:1]([O:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]1[CH:15]=[CH:16][N:17]([CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][O:19]2)[N:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 899628075-[(1S,2R)-2-(Benzyloxy)cyclopentyl]-1H-pyrazole

Product 1

HCID 899619363-[(1S,2R)-2-(Benzyloxy)cyclopentyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazoleYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 148d by using the 5-[(1S,2R)-2-(benzyloxy)cyclopentyl]-1H-pyrazole (320 mg, 1.32 mmol) prepared in Example 149a, 3,4-dihydro-2H-pyran (0.723 mL, 7.92 mmol), p-toluenesulfonic acid hydrate (50 mg, 0.266 mmol) and dichloromethane (5.0 mL), to yield the title compound (421 mg, 98%) in the form of a diastereomeric mixture as a colorless oil.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-3ba76bcf82db463a8d1a485b7ff169e6
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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