Triethylamine → tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylate

HRID 423640노트

반응식

HRID 423640 반응식
[NH:1]1[CH2:6][CH2:5][CH:4]([CH:7]([OH:9])[CH3:8])[CH2:3][CH2:2]1.[O:10](C(OC(C)(C)C)=O)[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=O.CCN(CC)CC>ClCCCl>[OH:9][CH:7]([CH:4]1[CH2:5][CH2:6][N:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:10])[CH2:2][CH2:3]1)[CH3:8]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 3383211-(Piperidin-4-yl)ethan-1-ol

생성물 1

HCID 21989903tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylate수율 93%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

(±)-1-(4-Piperidinyl)ethanol (see reference: WO 9725992A, 12.44 g, 65.7 mmol) in 1,2-dichloroethane (500 mL) was stirred at room temperature and BOC2O (14.36 g, 65.8 mmol) was added followed by Et3N (19 mL, 136 mmol). The stirred mixture was heated at gentle reflux for 15 min and then allowed to cool to room temperature and stirred overnight. The solution was washed twice with 10% citric acid, once with 10% Na2CO3, dried over MgSO4, filtered and concentrated to afford (±)-1,1-dimethylethyl 4-(1-hydroxyethyl)-1-piperidinecarboxylate (14 g, 93% yield) as a light amber oil. 1H NMR (400 MHz, DMSO-d6): δ 4.35 (d, 1H, J=4.8 Hz), 3.92 (m, 2H), 3.32 (m, 1H), 2.59 (m, 2H), 1.68 (m, 1H), 1.47 (m, 1H), 1.34 (s, 9H), 1.25 (m, 1H), 1.08-0.88 (m, 2H), 0.97 (d, 3H, J=6.4 Hz).

후처리

  1. temperatureThe stirred mixture was heated
  2. temperatureat gentle reflux for 15 min
  3. washThe solution was washed twice with 10% citric acid, once with 10% Na2CO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8e4caddd4a014e23a176eaaeb99c2806
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101634B2

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