Water → HCID 89963478, compound

HRID 337893Notes

Reaction equation

HRID 337893 reaction equation
[CH2:1]([O:8][C@@H:9]1[CH2:13][C@H:12]([OH:14])[C@@H:11]([C:15]2[N:19]([CH3:20])[N:18]=[CH:17][CH:16]=2)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:30][O:31][CH2:32]Cl.O>ClCCl>[CH2:1]([O:8][C@H:9]1[CH2:10][C@H:11]([C:15]2[N:19]([CH3:20])[N:18]=[CH:17][CH:16]=2)[C@@H:12]([O:14][CH2:30][O:31][CH3:32])[CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 89962749HCID 89962749, compound

Product 1

HCID 89963478HCID 89963478, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of the (1S*,2R*,4S*)-4-benzyloxy-2-(1-methyl-1H-pyrazol-5-yl)cyclopentanol (350 mg, 1.29 mmol) prepared in Example 98a and diisopropylethylamine (1.3 mL, 7.64 mmol) in dichloromethane (5.0 mL), chloromethyl methyl ether (0.48 mL, 6.32 mmol) was added, and the reaction solution was stirred at 40° C. for 5 hours. After allowing to cool, water (10 mL) was added to the reaction solution, and an organic layer was extracted. The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (hexane/ethyl acetate=1:2) to yield the title compound (250 mg, 62%) as a colorless oil.

Workup

  1. temperatureto cool
  2. extractionan organic layer was extracted
  3. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
  4. concentrationAfter vacuum concentration
  5. customthe residue was purified with silica gel chromatography (hexane/ethyl acetate=1:2)

Sources & evidence

ORD record
ord-026ec30f89cf4f5aa2dda761e68fe1ea
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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