Water → n-((s)-4-Chloro-9-(r,s)-hydroxy-1-methoxy-2-nitro-6,7,8,9-tetrahydro-5h-benzocyclohepten-7-yl)-acetamide

HRID 1041169노트

반응식

HRID 1041169 반응식
[Cl:1][C:2]1[C:12]2[CH2:11][CH2:10][C@H:9]([NH:13][C:14](=[O:16])[CH3:15])[CH2:8][C:7](=[O:17])[C:6]=2[C:5]([O:18][CH3:19])=[C:4]([N+:20]([O-:22])=[O:21])[CH:3]=1.[BH4-].[Na+].O>CO>[Cl:1][C:2]1[C:12]2[CH2:11][CH2:10][C@H:9]([NH:13][C:14](=[O:16])[CH3:15])[CH2:8][CH:7]([OH:17])[C:6]=2[C:5]([O:18][CH3:19])=[C:4]([N+:20]([O-:22])=[O:21])[CH:3]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 4311764Sodium borohydride2회HCID 57853797N-((S)-4-Chloro-1-methoxy-2-nitro-9-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-yl)-acetamide

생성물 1

HCID 131729599n-((s)-4-Chloro-9-(r,s)-hydroxy-1-methoxy-2-nitro-6,7,8,9-tetrahydro-5h-benzocyclohepten-7-yl)-acetamide

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

N-((S)-4-Chloro-1-methoxy-2-nitro-9-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-yl)-acetamide (100 mg; 0.3 mmol), of Example 632f, in Methanol (10 mL) was treated with Sodium tetrahydroborate (30 mg, 0.8 mmol) neat at rt. After 15 minutes, a second portion of Sodium tetrahydroborate (30 mg, 0.8 mmol) was added to the reaction mixture. After 30 minutes the reaction mixture was treated with water, then extract with Et2O followed by CH2Cl2 (2×). The aqueous phase was treated with 1N KOH and re-extracted with CH2Cl2. The organics were combined, dried over MgSO4, filtered and concentrated to give 210 mg (TW 100 mg) of whitish, crude N-((S)-4-Chloro-9-(R,S)-hydroxy-1-methoxy-2-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-yl)-acetamide, which was used without further purification; MS (m/e) 328.97 (M+H).

후처리

  1. extractionextract with Et2O
  2. additionThe aqueous phase was treated with 1N KOH
  3. extractionre-extracted with CH2Cl2
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e5ec667b3cb94fd98e527319691909fe
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552186B2

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