Sodium borohydride → HCID 57803061, compound

HRID 2102677Notes

Reaction equation

HRID 2102677 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13](=[C:16]2[C:24]3[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=3)[NH:18][C:17]2=[O:26])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>CO.O>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([CH:16]2[C:24]3[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=3)[NH:18][C:17]2=[O:26])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 57803050HCID 57803050, compound

Product 1

HCID 57803061HCID 57803061, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
40 °C

Procedure

Sodium borohydride (0.38 g, 10 mmol) (Aldrich) was added in small portions to a solution of 4-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidene)-piperidine-1-carboxylic acid tert-butyl ester (0.35 g, 1 mmol) (from Example 12a supra) in methanol (25 mL) and water (3 mL) at such a rate that gas evolution was not too vigorous. When addition was complete, mixture was heated at 40° C. for 1 hour. After cooling, mixture was slowly diluted with water. Precipitate formed was collected by filtration and washed with cold aqueous methanol to give rac-4-(6-chloro-2-oxo-2,3-dihydro-1H-indol-3-yl)-piperidine-1-carboxylic acid tert-butyl ester as a white crystalline material. (Yield 0.33 g, 94.0%).

Workup

  1. additionWhen addition
  2. temperatureAfter cooling
  3. customPrecipitate formed
  4. filtrationwas collected by filtration
  5. washwashed with cold aqueous methanol

Sources & evidence

ORD record
ord-a65d9e0485ee4997a9e235521b22aeff
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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