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

HRID 1687474노트

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HRID 1687474 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-1296f936526b499cb1a6d98c67d1dac4
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148391B2

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