(R)-1-N-BOC-PIPECOLAMIDE synthesis
- Product Name:(R)-1-N-BOC-PIPECOLAMIDE
- CAS Number:848488-91-5
- Molecular formula:C11H20N2O3
- Molecular Weight:228.29
28697-17-8
848488-91-5
Step B. Synthesis of tert-butyl (2R)-2-(aminocarbonyl)piperidine-1-carboxylate: To a mixture of (2R)-1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid (2.29 g, 10 mmol), ammonium chloride (3.21 g, 60 mmol), and DMF (70 mL) was added HATU (5.60 g, 14.7 mmol) at 0 °C and DIPEA (3.88 g, 30 mmol). The reaction mixture was stirred at room temperature for 18 hours. After completion of the reaction, the reaction solution was diluted with H2O (100 mL) and extracted with EtOAc (3 x 100 mL). The organic phases were combined and washed sequentially with 10% Na2CO3 solution (2 × 30 mL), brine (2 × 30 mL) and then dried with Na2SO4. After filtration and concentration, it was purified by MPLC on silica gel using hexane/EtOAc (1:1) as eluent to afford R-N-Boc-prolinamide as a white solid.1H NMR (400 MHz, CDCl3) δ: 1.46 (s, 9H), 1.63 (m, 2H), 2.22 (m, 1H), 2.91 (m, 1H), 3.06 (m, 3H), 4.01 (m, 1H), 4.71 (m, 1H), 6.46 (br, 2H).MS (ESI) m/z: 228.92 (M+H)+.
28697-17-8
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848488-91-5
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Yield:848488-91-5 100%
Reaction Conditions:
with ammonium chloride;N-ethyl-N,N-diisopropylamine;HATU in DMF (N,N-dimethyl-formamide) at 0 - 20; for 18 h;
Steps:
77.B
Step B. tert-Butyl (2R)-2-(aminocarbonyl)piperidine-1-carboxylate; HATU (5.60 g, 14.7 mmol) was added to a mixture of the (2R)- 1 -(tert- butoxycarbonyl) piperidine-2-carboxylic acid (2.29 g, 10 mmol), ammonium chloride (3.21 g, 60 mmol) and DIPEA (3.88 g, 30 mmol) in DMF (70 mL) at 0 °C. The mixture was stirred for 18 h at room temperature, diluted with H20 (100 mL) and extracted with EtOAc (3x100 mL). The combined organic phases were washed with 10% Na2C03 solution (2x30 mL), brine (2x30 mL) and dried with Na2S04. After filtration and concentration, the title compound was purified by MPLC on silica gel using hexane/EtOAc (1:1) g, 100 %) as a white solid. (at)H NMR(400 MHz, CDCl3) No. 1.46 (s, 9 H), 1.63 (m, 2 H), 2.22 (m, 1 H), 2.91 (m, 1 H), 3.06 (m, 3 H), 4.01 (m, 1 H), 4.71 (m, 1 H), 6.46 (s broad, 2 H). MS (ESI) (M+H) (at)= 228.92
References:
WO2005/115986,2005,A1 Location in patent:Page/Page column 103