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

HRID 1687474Notes

Reaction equation

HRID 1687474 reaction equation
[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

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydride2×HCID 57853797N-((S)-4-Chloro-1-methoxy-2-nitro-9-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-yl)-acetamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-1296f936526b499cb1a6d98c67d1dac4
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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