N-Boc-2-piperidinecarboxylic acid synthesis
- Product Name:N-Boc-2-piperidinecarboxylic acid
- CAS Number:98303-20-9
- Molecular formula:C11H19NO4
- Molecular Weight:229.27
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Yield:98303-20-9 99%
Reaction Conditions:
Stage #1: di-tert-butyl dicarbonate;piperidine-2-carboxylic acidwith potassium carbonate in lithium hydroxide monohydrate;propan-2-one at 20;
Stage #2: with hydrogenchloride in lithium hydroxide monohydrate;propan-2-one; pH=~ 3;
Steps:
18 Example 18; Piperidine-1,2-dicarboxylic acid-1-tert-butyl ester
A solution of DL-pipecolinic acid (13 g, 100 mmol), potassium carbonate (55.2 g, 400 mmol), di-tert-butyl dicarbonate (28. 4 g, 130 mmol) in acetone (30 mL) and water (100 mL) was stirred at room temperature overnight. The reaction mixture was brought to [PH-] 3 using hydrochloric acid (1 N aqueous) and then extracted with ethyl acetate (350 mL). The organic phase was separated, sequentially washed with water (200 mL) and brine (200 mL), dried (sodium sulfate), filtered and concentrated in vacuo. The isolated solid was triturated with hexanes to yield 22.7 g (99%) of the title compound as a white [SOLID. LH-] NMR [(CDC13),] [8] [(PPM)] : 9.3 (bs, 1H), 4.84 (bd, 1H), 3.94 (m, 1H), 2.93 (m, 1H), 2.22 (m, 1H), 1.67 (m, 3H), 1.45 (m, [11H).]
References:
WO2004/14902,2004,A2 Location in patent:Page 45
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