Water → HCID 89962871, compound
Reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11]([C@H:12]2[CH2:16][CH2:15][CH2:14][C@@H:13]2[OH:17])=[CH:10][CH:9]=[N:8]1.[H-].[Na+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C=O)C>[CH2:20]([O:17][C@H:13]1[CH2:14][CH2:15][CH2:16][C@@H:12]1[C:11]1[N:7]([CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[N:8]=[CH:9][CH:10]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1Participants
6
Procedure
To a solution of the (1S*,2R*)-2-[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl]cyclopentanol (975 mg, 4.13 mmol) prepared in Example 138a in DMF (20 mL), sodium hydride (63%; 236 mg, 6.19 mmol) and benzyl bromide (0.735 mL, 6.19 mmol) were added, and the reaction solution was stirred at room temperature for 7 hours. To the reaction solution, water (50 mL) was added, followed by extraction with ethyl acetate (50 mL). The thus obtained organic layer was washed twice with water (50 mL) and dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (hexane/ethyl acetate=7:3) to yield the title compound (1.15 g, 57%) in the form of a diastereomeric mixture as a colorless oil.
Workup
- extractionfollowed by extraction with ethyl acetate (50 mL)
- washThe thus obtained organic layer was washed twice with water (50 mL)
- dry with materialdried over anhydrous sodium sulfate
- concentrationAfter vacuum concentration
- customthe residue was purified with silica gel chromatography (hexane/ethyl acetate=7:3)
Sources & evidence
- ORD record
- ord-6ad1a897b7224f8cb10404b69fb6312b
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889741B2
Reaction notes
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