Tert-butyl 4-[4-(benzyloxy)phenoxy]piperidine-1-carboxylate → Tert-butyl 4-hydroxypiperidine-1-carboxylate
Reaction equation
C(OC1C=CC([O:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)=CC=1)C1C=CC=CC=1>[Pd].C(O)C>[C:23]([O:22][C:20]([N:17]1[CH2:18][CH2:19][CH:14]([OH:13])[CH2:15][CH2:16]1)=[O:21])([CH3:26])([CH3:24])[CH3:25]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To 10% palladium on carbon (0.75 g), under a stream of argon, was added a solution of tert-butyl 4-[4-(benzyloxy)phenoxy]piperidine-1-carboxylate (7.5 g) in ethanol (250 mL). The vessel was purged with argon three times, before hydrogen was introduced to the system via a balloon. The reaction was stirred vigorously at ambient temperature for 3 hours. Hydrogen was removed from the system and purged three times with argon before filtering through a celite pad. The pad was washed thoroughly. The filtrate and washings were combined and evaporated, the solid triturated with 20% diethyl ether/iso-hexane to yield tert-butyl-4-hydroxy-1-piperidinecarboxylate (5.7 g) NMR Spectrum: (CDCl3) 1.5 (s, 9H), 1.7 (m, 2H), 1.9 (m, 2H), 3.3 (m, 2H), 3.7 (m, 2H), 4.3 (m, 1H), 4.8 (s, 1H), 6.7 (m, 4H).
Workup
- customThe vessel was purged with argon three times, before hydrogen
- additionwas introduced to the system via a balloon
- customHydrogen was removed from the system
- custompurged three times with argon
- filtrationbefore filtering through a celite pad
- washThe pad was washed thoroughly
- customevaporated
- customthe solid triturated with 20% diethyl ether/iso-hexane
Sources & evidence
- ORD record
- ord-7842ac2aeda64b11a0752fec74ff25b4
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129412B2
Reaction notes
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