[1-(3-tert-Butoxycarbonylamino-propyl)-piperidin-4-yl]-carbamic acid benzyl ester → tert-Butyl (3-(4-aminopiperidin-1-yl)propyl)carbamate
Reaction equation
C(OC(=O)[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:13][CH2:12]1)C1C=CC=CC=1>C(O)C.[Pd]>[C:24]([O:23][C:21](=[O:22])[NH:20][CH2:19][CH2:18][CH2:17][N:14]1[CH2:15][CH2:16][CH:11]([NH2:10])[CH2:12][CH2:13]1)([CH3:27])([CH3:25])[CH3:26]Participants
Conditions
- Temperature
- 23 °C
Procedure
To a solution of [1-(3-tert-butoxycarbonylamino-propyl)-piperidin-4-yl]-carbamic acid benzyl ester (16.9 g, 43.2 mmol, 1 equiv) in ethanol (200 mL) at 23° C. was added palladium on carbon (2.25 g, 10 wt. %, wet, Degussa type). The reaction vessel was placed under an atmosphere of hydrogen (balloon) and stirred for 14 h. At this time tlc analysis indicated the reaction was incomplete, the mixture was filtered through a pad of Celite, washing with ethanol (100 mL). The resulting solution was treated with fresh palladium catalyst (2.25 g), then placed under an atmosphere of hydrogen (balloon) at 50° C. After 7 h tlc analysis indicates complete consumption of the starting material. The reaction mixture was cooled to 23° C., and then filtered through Celite, washing with ethanol (200 mL). The filtrate was concentrated to give 11.1 g (43.2 mmol, 100%) of the desired compound.
Workup
- filtrationthe mixture was filtered through a pad of Celite
- washwashing with ethanol (100 mL)
- additionThe resulting solution was treated with fresh palladium catalyst (2.25 g)
- customplaced under an atmosphere of hydrogen (balloon) at 50° C
- waitAfter 7 h
- customconsumption of the starting material
- filtrationfiltered through Celite
- washwashing with ethanol (200 mL)
- concentrationThe filtrate was concentrated
Sources & evidence
- ORD record
- ord-966589f2882d4b0c9fdd7de3d1ac4dd2
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09023843B2
Reaction notes
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