Lithium Hydroxide → 2-(Cyclohexylmethyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid

HRID 1963128노트

반응식

HRID 1963128 반응식
[CH:1]1([CH2:7][CH:8]2[CH2:13][CH:12]([C:14]([O:16]C)=[O:15])[CH2:11][CH2:10][N:9]2[C:18]([O:20][CH3:21])=[O:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].[OH-]>C1COCC1.O>[CH:1]1([CH2:7][CH:8]2[CH2:13][CH:12]([C:14]([OH:16])=[O:15])[CH2:11][CH2:10][N:9]2[C:18]([O:20][CH3:21])=[O:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 86646598Dimethyl 2-(cyclohexylmethyl)piperidine-1,4-dicarboxylate

생성물 1

HCID 667322852-(Cyclohexylmethyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Dimethyl 2-(cyclohexylmethyl)piperidine-1,4-dicarboxylate (2.20 g, 7.40 mmol) was dissolved in THF (25 mL) and water (25 mL). LiOH (0.266 g, 11.1 mmol) was added and the resulting mixture was stirred at room temperature overnight and heated under reflux for 30 min. The reaction mixture was partitioned between 1 M KHSO4 and diethyl ether. The organic phase was dried (Na2SO4), filtered through Celite® and the solvent was evaporated. The crude product was dissolved again in THF (25 mL) and water (25 mL). LiOH (0.23 g) was added to the reaction flask. The reaction mixture was stirred overnight. The reaction was worked up as above to give the product. 1H NMR (600 MHz, cdcl3) δ 0.85 (ddd, 2H), 1.19 (dddd, 5H), 1.38-1.48 (m, 1H), 1.61 (d, 4H), 1.72 (tt, 2H), 1.97 (qd, 3H), 2.56-2.65 (m, 1H), 3.02-3.14 (m, 1H), 3.67 (d, 3H), 3.88 (d, 1H), 4.22 (s, 1H).

후처리

  1. temperatureheated
  2. temperatureunder reflux for 30 min
  3. customThe reaction mixture was partitioned between 1 M KHSO4 and diethyl ether
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered through Celite®
  6. customthe solvent was evaporated
  7. dissolutionThe crude product was dissolved again in THF (25 mL)
  8. additionLiOH (0.23 g) was added to the reaction flask
  9. stirringThe reaction mixture was stirred overnight
  10. customto give the product

출처 및 근거

ORD 기록
ord-575fbe7982bb4b10ab8da3783db3f2bd
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415378B2

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