Acetic Acid → HCID 14371630、化合物

HRID 1464006ノート

反応式

HRID 1464006 の反応式
[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

参加物

5

反応物 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 14371625HCID 14371625、化合物

生成物 1

HCID 14371630HCID 14371630、化合物収率 53%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-955988b28661424babf52ac658a2ad04
出典データセット
uspto-grants-1994_04
特許番号
US05302716

反応ノート

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