Sodium borohydride → HCID 57803051, compound

HRID 2102737Notes

Reaction equation

HRID 2102737 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:16][CH2:15][CH2:14][C:13](=[C:17]2[C:25]3[C:20](=[CH:21][C:22]([Cl:26])=[CH:23][CH:24]=3)[NH:19][C:18]2=[O:27])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>CO.O>[C:3]([O:7][C:8]([N:10]1[CH2:16][CH2:15][CH2:14][CH:13]([CH:17]2[C:25]3[C:20](=[CH:21][C:22]([Cl:26])=[CH:23][CH:24]=3)[NH:19][C:18]2=[O:27])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 68858354HCID 68858354, compound

Product 1

HCID 57803051HCID 57803051, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium borohydride (1.42 g, 37.5 mmol) (Aldrich) was added in small portions to a solution of rac-4-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidene)-azepane-1-carboxylic acid tert-butyl ester (1.36 g, 3.75 mmol) (from Example 61a supra) in methanol (25 mL) and water (0.5 mL). After stirring at room temperature for 30 minutes, the reaction mixture was concentrated. The residue was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate three times. The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated to give rac-4-(6-chloro-2-oxo-2,3-dihydro-1H-indol-3-yl)-azepane-1-carboxylic acid tert-butyl ester as a white solid (Yield 1.37 g, 100%).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe residue was partitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted with ethyl acetate three times
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ece532634c85468c80438ad63b8d4d51
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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