Methanol → methyl (R)-piperidine-2-carboxylate

HRID 1776681

반응식

HRID 1776681 반응식
[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]

참가 물질

4

반응물 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 736316Pipecolic acid, (+)-

생성물 1

HCID 7408456methyl (R)-piperidine-2-carboxylate수율 92%

반응 조건

온도
0 °C

실험 절차

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).

후처리

  1. customat RT overnight, evaporated
  2. customcrystallized with EtOH/hexane

출처 및 근거

ORD 기록
ord-006241e5df52412c80179a06231046b7
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265841B2

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