Methanol → methyl (R)-piperidine-2-carboxylate
Reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C@@H:2]1[C:7]([OH:9])=[O:8].S(Cl)(Cl)=O.[CH3:14]O>>[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C@@H:2]1[C:7]([O:9][CH3:14])=[O:8]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
To (R)-Piperidine-2-carboxylic acid (5.00 g, 38.73) in 150 ml of dry methanol at 0° C. was added thionyl chloride (5.2 ml, 71.28 mmol) under Ar. The mixture was stirred at 0° C. for 30 min, then at RT overnight, evaporated and crystallized with EtOH/hexane to afford 4.96 g (92%) of the title product. 1H NMR (CD3OD) 3.67 (s, 3H), 3.57 (m, 1H), 2.79 (m, 1H), 2.69 (m, 1H), 2.01 (m, 1H), 1.98 (m, 1H), 1.73 (m, 1H), 1.55- 1.45 (m, 4H); 13C NMR 171.22, 62.50, 51.35, 45.35, 29.52, 28.41, 23.82; MS m/z+ 144.0 (M+H).
Workup
- customat RT overnight, evaporated
- customcrystallized with EtOH/hexane
Sources & evidence
- ORD record
- ord-c40ecf01d27040ed826c786613761485
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08426402B2
Reaction notes
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