Ethyl Acetate → tert-Butyl 4-{[(4-{[1-(hydroxymethyl)cyclopentyl]methoxy}-1,2-benzisoxazol-3-yl)oxy]methyl}-piperidine-1-carboxylate

HRID 2410387노트

반응식

HRID 2410387 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1([CH2:16][O:17][C:18]2[C:23]3[C:24]([O:27][CH2:28][CH:29]4[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]4)=[N:25][O:26][C:22]=3[CH:21]=[CH:20][CH:19]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1)=O.C(OCC)(=O)C>C(OCC)C>[OH:8][CH2:9][C:11]1([CH2:16][O:17][C:18]2[C:23]3[C:24]([O:27][CH2:28][CH:29]4[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]4)=[N:25][O:26][C:22]=3[CH:21]=[CH:20][CH:19]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 69320362HCID 69320362, 화합물

생성물 1

HCID 86622737tert-Butyl 4-{[(4-{[1-(hydroxymethyl)cyclopentyl]methoxy}-1,2-benzisoxazol-3-yl)oxy]methyl}-piperidine-1-carboxylate수율 81%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a suspension of lithium aluminum hydride (50.7 mg, 1.34 mmol) in diethyl ether (5 mL) was added an ethereal solution (3 mL) of tert-butyl 4-{[(4-{[1-(methoxycarbonyl)cyclopentyl]methoxy}-1,2-benzisoxazol-3-yl)oxy]methyl}piperidine-1-carboxylate (EXAMPLE 51, step 2, 600 mg, 1.23 mmol) at 0° C. After being stirred for 30 min, ethyl acetate was added to the mixture. Then the mixture was washed with 2N hydrochloric acid and brine. The organic layer was dried over magnesium sulfate and concentrated in vacuo to afford 456 mg (81%) of the title compound as a white solid. The crude product was used in the next step without further purification.

후처리

  1. washThen the mixture was washed with 2N hydrochloric acid and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-bdce677457394fc4803ebd38d0767b58
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08816090B2

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