Acetic Acid → HCID 14371630, 화합물

HRID 1464006노트

반응식

HRID 1464006 반응식
[CH3:1][O:2][C:3]1[C:4]([Cl:21])=[CH:5][C:6]2[CH:12]=[CH:11][NH:10][C@@H:9]3[CH2:13][C:14]4[C:19]([C@H:8]3[C:7]=2[CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=4.C([BH3-])#N.[Na+].C(O)(=O)C>C(O)C>[CH3:1][O:2][C:3]1[C:4]([Cl:21])=[CH:5][C:6]2[CH2:12][CH2:11][NH:10][C@@H:9]3[CH2:13][C:14]4[C:19]([C@H:8]3[C:7]=2[CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=4

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 14371625HCID 14371625, 화합물

생성물 1

HCID 14371630HCID 14371630, 화합물수율 53%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

The crude Compound N from step D was dissolved in 20 mL absolute ethanol and treated with 0.12 grams (1.91 mmol) sodium cyanoborohydride. To this was added 0.108 mL glacial acetic acid, and the mixture was stirred at room temperature for 3 hours. The reaction was quenched with 10 mL 1M HCl and stirred for 30 minutes. The reaction was made basic with 30% NaOH and extracted into 250 mL ethyl actetate. The organic layer was dried (MgSO4) and evaporated to give 350 mg (53%) of trans-5,6,7,7a,8,12b-hexahydro-2-methoxy-3-chlorobenz[d]indeno[2,1-b]azepine (Compound P) as an oil, 200 MHz NMR (CDCl3) d 3.60-3.85(m,3H), 3.10-3.40(m,4H), 3.71(s,3H), 4.54(d,1H,J=8 Hz), 7.07(s,1H), 7.16(s,1H), 7.20-7.40(m,4H).

후처리

  1. customThe reaction was quenched with 10 mL 1M HCl
  2. stirringstirred for 30 minutes
  3. extractionextracted into 250 mL ethyl actetate
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated

출처 및 근거

ORD 기록
ord-955988b28661424babf52ac658a2ad04
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05302716

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