Benzyl 4-((1R,2S)-2-(2-hydroxyethyl)cyclopropyl)piperidine-1-carboxylate → 2-((1S,2R)-2-(piperidin-4-yl)cyclopropyl)ethanol
Reaction equation
[OH:1][CH2:2][CH2:3][C@@H:4]1[CH2:6][C@@H:5]1[CH:7]1[CH2:12][CH2:11][N:10](C(OCC2C=CC=CC=2)=O)[CH2:9][CH2:8]1>[Pd].CO>[NH:10]1[CH2:11][CH2:12][CH:7]([C@H:5]2[CH2:6][C@H:4]2[CH2:3][CH2:2][OH:1])[CH2:8][CH2:9]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Benzyl 4-((1R,2S)-2-(2-hydroxyethyl)cyclopropyl)piperidine-1-carboxylate (7.50 g, 24.7 mmol) and palladium on activated carbon (10%, wet, 1.00 g) in methanol (130 mL) were stirred under an atmosphere of hydrogen (1 atm) at RT for 48 h. The mixture was filtered through Celite® and the filter cake washed with methanol. The filtrate was concentrated to dryness under reduced pressure to afford the compound as a white solid. 1H NMR (500 MHz, CDCl3) δ 3.74 (m, 2H), 3.15-3.05 (m, 2H), 2.56 (m, 2H), 1.91-1.87 (m, 2H), 1.76-1.72 (m, 3H), 1.36-1.28 (m, 3H), 0.92-0.87 (m, 1H), 0.84-0.76 (m, 1H), 0.67-0.61 (m, 1H), 0.60-0.56 (m, 1H), −0.18 (q, J=4.5 Hz, 1H).
Workup
- filtrationThe mixture was filtered through Celite®
- washthe filter cake washed with methanol
- concentrationThe filtrate was concentrated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-1ac4d2e4284d4f41b5273c954d9cca56
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08957062B2
Reaction notes
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