(+/-)-TRANS-N-BOC-4-METHYL-PIPECOLINIC ACID synthesis

6synthesis methods

Product Name:(+/-)-TRANS-N-BOC-4-METHYL-PIPECOLINIC ACID
CAS Number:123811-83-6
Molecular formula:C12H21NO4
Molecular Weight:243.3

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(+/-)-TRANS-N-BOC-4-METHYL-PIPECOLINIC ACID

123811-83-6
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Yield:123811-83-6 89%

Reaction Conditions:

Stage #1: 4-methylpiperidine-1-carboxylic acid tert-butyl esterwith N,N,N,N,-tetramethylethylenediamine;sec.-butyllithium in diethyl ether;cyclohexane at -78 - 20; for 1 h;
Stage #2: carbon dioxide in diethyl ether;cyclohexane at -78; for 0.25 h;

Steps:

6 Preparation of compound 55

A solution of compound 54 (926.5 mg, 5.0 mmol) in Et₂O (10.5 mL) was cooled to -78°C and treated with TMEDA (755 μL, 5.0 mmol) followed by slow addition of a 1.3 M cyclohexane solution of sec-butyllithium (4.6 mL, 6.0 mmol) over a 30 minute period. The reaction solution was then warmed to -20°C and maintained at that temperature for 30 minutes, after which the solution was re-cooled to -78°C and purged with gaseous carbon dioxide for 15 minutes. The reaction solution was then slowly warmed to 0°C and poured into a biphasic mixture of 1 N HCl (100 mL) and EtOAc (50 mL). The reaction solution was then extracted several times with EtOAc. The EtOAc extracts were combined, dried over Mg₂SO₄, filtered, and concentrated to provide compound 55 (1.07 g) in 89% yield as a colorless oil (a mixture of two cis enantiomers).

References:

EP2374454,2016,B1 Location in patent:Paragraph 0133; 0134