Sodium borohydride → HCID 86682431, 화합물

HRID 715898노트

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HRID 715898 반응식
[F:1][C:2]1([F:56])[CH2:7][CH2:6][CH:5]([C:8]2[C:17]3[CH:16]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=4)[CH2:15][C:14]([CH3:29])([CH3:28])[CH2:13][C:12]=3[N:11]=[C:10]([CH:30]3[CH2:35][CH2:34][N:33]([C:36]4[N:41]=[CH:40][C:39]([CH:42]=[O:43])=[CH:38][N:37]=4)[CH2:32][CH2:31]3)[C:9]=2[CH:44]([F:55])[C:45]2[CH:50]=[CH:49][C:48]([C:51]([F:54])([F:53])[F:52])=[CH:47][CH:46]=2)[CH2:4][CH2:3]1.[BH4-].[Na+]>C(O)C.O1CCCC1>[F:56][C:2]1([F:1])[CH2:7][CH2:6][CH:5]([C:8]2[C:17]3[CH:16]([O:18][CH2:19][C:20]4[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=4)[CH2:15][C:14]([CH3:28])([CH3:29])[CH2:13][C:12]=3[N:11]=[C:10]([CH:30]3[CH2:31][CH2:32][N:33]([C:36]4[N:41]=[CH:40][C:39]([CH2:42][OH:43])=[CH:38][N:37]=4)[CH2:34][CH2:35]3)[C:9]=2[CH:44]([F:55])[C:45]2[CH:46]=[CH:47][C:48]([C:51]([F:52])([F:54])[F:53])=[CH:49][CH:50]=2)[CH2:4][CH2:3]1

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 866824324-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-2-[1-(5-formylpyrimidin-2-yl)piperidin-4-yl]-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-5,6,7,8-tetrahydroquinoline

생성물 1

HCID 86682431HCID 86682431, 화합물수율 103.8%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 500 mg (0.64 mmol) of 4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-2-[1-(5-formyl pyrimidin-2-yl)piperidin-4-yl]-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-5,6,7,8-tetrahydroquinoline, which was prepared by a method similar to that of Reference Example 16, in a mixture of 5 ml ethanol and 5 ml tetrahydrofuran, 12 mg (0.32 mmol) of sodium borohydride was added under ice cooling, and the reaction solution was stirred under ice cooling conditions for 0.83 hour. After completion of the reaction, the solvent was distilled off under reduced pressure and 1 N hydrochloric acid and 1 N sodium hydroxide aqueous solution were added in order, and the reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution and dried with anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to provide 0.52 g of the title compound as a white foam (yield: quantitative).

후처리

  1. additionwas added under ice cooling
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure and 1 N hydrochloric acid and 1 N sodium hydroxide aqueous solution
  4. additionwere added in order
  5. extractionthe reaction solution was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated sodium chloride aqueous solution
  7. dry with materialdried with anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-7f7844c7bb72432393d902a1e543b921
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187450B2

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