Sodium Hydroxide → Tert-butyl 4-(hydroxymethyl)-4-phenylpiperidine-1-carboxylate

HRID 391368노트

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HRID 391368 반응식
CC1C=CC(S(O)(=O)=O)=CC=1.[C:12]1([C:18]2([C:24]([OH:26])=O)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O1CCCC1.B.[C:33](=O)([O:39]C(C)(C)C)[O:34][C:35]([CH3:38])([CH3:37])[CH3:36].[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[OH:26][CH2:24][C:18]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:19][CH2:20][N:21]([C:33]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:39])[CH2:22][CH2:23]1

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 27236574-Piperidinecarboxylic acid, 4-phenyl-, 4-methylbenzenesulfonate (1:1)HCID 2723981Borane;tetrahydrofuranHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

생성물 1

HCID 9994433Tert-butyl 4-(hydroxymethyl)-4-phenylpiperidine-1-carboxylate수율 63%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

4-Phenyl-4-piperidinecarboxylic acid p-methylbenzenesulfonate (19.0 g, 50.3 mmol) was suspended in dry tetrahydrofuran (100 mL) and cooled to 0° C. To this was added borane tetrahydrofuran complex (1 M in THF, 100 mL, 100 mmol) cautiously over 15 min and the reaction mixture allowed to warm to room temperature overnight. The reaction mixture was cooled to 0° C., treated with di-tert-butyl carbonate (15.0 g, 218 mmol) and 10 N sodium hydroxide (12 mL), stirred at 0° C., and at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with water (2×), brine (2×), dried over sodium sulfate and concentrated. The crude product was triturated with 10% ethyl acetate/hexanes solution to afford 9.2 g (63%) of the title compound. 1H-NMR (CD3OD, 300 MHz) δ 7.35-7.43 (m, 4H), 7.24-7.26 (m, 1H), 3.78-3.85 (m, 2H), 3.49 (s, 2H), 2.97 (m, 2H), 2.17-2.21 (m, 2H), 1.77-1.87 (m, 2H), 1.46 (s, 9H). Mass spec.: 292.17 (MH)+.

후처리

  1. temperatureto warm to room temperature overnight
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. customat room temperature
  4. customovernight
  5. washwashed with water (2×), brine (2×)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe crude product was triturated with 10% ethyl acetate/hexanes solution

출처 및 근거

ORD 기록
ord-1181d0a93e5a4b7ca0e44474f8d98074
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383821B2

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