Diethyl Ether → 1-t-Butoxycarbonyl-4-(2-cyclopentyl-2-hydroxyethyl)piperidine
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14]I)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])(C)(C)C.[C:21]1(=O)[CH2:25][CH2:24][CH2:23][CH2:22]1.[NH4+].[Cl-].C[CH2:30][O:31]CC>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH:30]([CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[OH:31])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
Procedure
To a solution of 1.36 g (4.2 mmol) of 1-t-butoxycarbonyl-4-iodomethylpiperidine in 40 mL of ether at −78° C. was carefully added 5.8 mL (9.35 mmol) of t-butyl lithium (1.7 N on pentane). After stirring for 30 min, to the reaction mixture was added dropwise 0.95 mL (10.73 mmol) of cyclopentanone and the reaction mixture was stirred at −78° C. for 2 h. To the reaction mixture was added 5 mL of sat'd NH4Cl solution and the reaction mixture was warmed to rt. The reaction mixture was partitioned between sat'd NH4Cl solution and ether. The aqueous fraction was extracted with ether and the combined organic fractions were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ether, 4:1) to give 0.36 g of the title compound.
Workup
- customat −78° C.
- stirringthe reaction mixture was stirred at −78° C. for 2 h
- customThe reaction mixture was partitioned between sat'd NH4Cl solution and ether
- extractionThe aqueous fraction was extracted with ether
- washthe combined organic fractions were washed with sat'd NaCl solution
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationthe filtrate was concentrated
- customThe residue was purified by chromatography (silica, hexanes:ether, 4:1)
Sources & evidence
- ORD record
- ord-f799b7bf98ca4e61a1c807b9fe88282d
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06455548B2
Reaction notes
Loading…