Sodium borohydride → 3-Benzyl-1,2,3,4,5,6-hexahydro-7h-pyrido[3,4-d][2]benzazepin-7-one

HRID 1035302노트

반응식

HRID 1035302 반응식
[Br-].[CH2:2]([N+:9]1[CH:19]=[CH:18][C:17]2[C:16]3[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=3[C:14](=[O:24])[NH:13][CH2:12][C:11]=2[CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+]>C(O)C.O>[CH2:2]([N:9]1[CH2:19][CH2:18][C:17]2[C:16]3[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=3[C:14](=[O:24])[NH:13][CH2:12][C:11]=2[CH2:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 672477733-Benzyl-7-oxo-6,7-dihydro-5h-pyrido[3,4-d][2]benzazepin-3-ium bromide

생성물 1

HCID 595485223-Benzyl-1,2,3,4,5,6-hexahydro-7h-pyrido[3,4-d][2]benzazepin-7-one

시약·촉매·용매 1

HCID 19096565Water ethanol용매

실험 절차

To a suspension of Example 180E (17.7 g, 46.4 mmol) in 200 mL of ethanol/water (4:1) at 0° C. was added NaBH4 (8.9 g, 0.232 mol) portion-wise. After stirring for 0.5 hour, the mixture was quenched with 1 N HCl to pH 4-5 and concentrated under reduced pressure. The residue was dissolved in 100 mL of saturated aqueous K2CO3 and extracted with dichloromethane. The organic phase was washed with brine, dried and purified by column chromatography on silica gel eluting with dichloromethane/methanol (30:1) to obtain the title compound.

후처리

  1. customthe mixture was quenched with 1 N HCl to pH 4-5
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 100 mL of saturated aqueous K2CO3
  4. extractionextracted with dichloromethane
  5. washThe organic phase was washed with brine
  6. customdried
  7. custompurified by column chromatography on silica gel eluting with dichloromethane/methanol (30:1)

출처 및 근거

ORD 기록
ord-dfc17fbe992e4893892e01946691a99d
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546377B2

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