Triethylamine → (R)-1-Ethylcarbamoylpiperidine-2-carboxylic acid

HRID 1923411노트

반응식

HRID 1923411 반응식
[CH2:1]1[CH2:6][C@@H:5]([C:7]([OH:9])=[O:8])[NH:4][CH2:3][CH2:2]1.[CH2:10]([N:12]([CH2:15]C)CC)[CH3:11].ClC(OCC)=[O:19]>ClCCl>[CH2:10]([NH:12][C:15]([N:4]1[CH2:3][CH2:2][CH2:1][CH2:6][C@@H:5]1[C:7]([OH:9])=[O:8])=[O:19])[CH3:11]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 439227Pipecolic acid, (-)-

생성물 1

HCID 54508361(R)-1-Ethylcarbamoylpiperidine-2-carboxylic acid수율 77%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

L-Pipecolinic acid (0.50 g, 0.004 mole) in dry dichloromethane (10 ml) was cooled to 0° C. under argon and treated with triethylamine (0.65 ml. 0.0046 mole) followed dropwise by ethyl chloroformate (0.37 ml, 0.004 mole) in dry dichloromethane (2 ml). The mixture was stirred overnight at room temperature after which it was diluted with dichioromethane, washed with 5M hydrochloric acid and the organic layer dried (magnesium sulfate) and evaporated in vacuo to afford the title compound 0.60 g (77%) as an orange oil; 1H NMR (CDCl3) 1.12-1.84 (8H, m), 2.15-2.40 (1H, m), 2.88-3.20 (1H, m), 3.90-4.28 (3H, m), 4.77-5.07 (1H, m), 5.68-6.82 (1H, br s),

후처리

  1. washwashed with 5M hydrochloric acid
  2. dry with materialthe organic layer dried (magnesium sulfate)
  3. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-903349845f3f4569a87c01d2b7cb9227
출처 데이터셋
uspto-grants-2012_05
특허 번호
USRE043390E1

반응 노트

불러오는 중…