Acetic Acid → tert-Butyl 4-[(prop-2-en-1-yl)amino]piperidine-1-carboxylate
Reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].C(O)(=O)C.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]([NH:4][CH:19]1[CH2:20][CH2:21][N:16]([C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15])[CH2:17][CH2:18]1)[CH:2]=[CH2:3]Participants
Procedure
Allylamine (0.45 mL, 0.34 g, 6.0 mmol), acetic acid (0.300 mL, 315 mg, 5.24 mmol), and 3 Å molecular sieves (2.00 g) were added to a solution of 1-(tert-butyoxycarbonyl)-4-piperidone (1.00 g, 5.01 mmol) in 14 mL of 1,2-dichloroethane. After stirring 0.5 h at RT, sodium triacetoxyborohydride (1.62 g, 7.6 mmol) was added in two portions 5 min apart. After an additional 3 h, the mixture was partitioned between 30 mL of ethyl acetate and 20 mL of saturated aqueous sodium bicarbonate. The aqueous layer was extracted with 30 mL of ethyl acetate and the organic layers were washed in succession with 20 mL of brine, combined, dried over sodium sulfate, and evaporated to give 1.20 g of crude 4-(allylamino)-1-(tert-butoxycarbonyl)piperidine as a yellow syrup.
Workup
- waitAfter an additional 3 h
- customthe mixture was partitioned between 30 mL of ethyl acetate and 20 mL of saturated aqueous sodium bicarbonate
- extractionThe aqueous layer was extracted with 30 mL of ethyl acetate
- washthe organic layers were washed in succession with 20 mL of brine
- dry with materialdried over sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-5c26dc48c93e45afba2fa331a3444daa
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06476054B1
Reaction notes
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