Sodium borohydride → HCID 58495491, compound

HRID 1191059Notes

Reaction equation

HRID 1191059 reaction equation
[CH3:1][C:2]([CH3:17])([CH3:16])[CH2:3][S:4]([CH2:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1)(=[O:6])=[O:5].[BH4-].[Na+]>CO.O.O.O.O.O.O.O.[Co](Cl)Cl>[CH3:1][C:2]([CH3:17])([CH3:16])[CH2:3][S:4]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:12][NH2:13])=[CH:14][CH:15]=1)(=[O:6])=[O:5]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 58495604HCID 58495604, compound

Product 1

HCID 58495491HCID 58495491, compoundYield 49%

Reagents, catalysts & solvents 3

HCID 517166Dichlorocobalt hexahydrateCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Add cobalt(II) chloride hexahydrate (1.83 mg, 7.7 mmol) to a solution of 4-(2,2-dimethylpropane-sulfonylmethyl)-benzonitrile (966 mg, 3.85 mmol) in methanol (25 mL). Cool the mixture to 0° C. and stir for 15 min. Carefully add sodium borohydride (1.46 g, 38.49 mmol) in small batches, allow the mixture to warm to room temperature and stir for 2 h. Dilute the mixture with water and partition between water and chloroform. Extract the aqueous phase three times with chloroform/iso-propanol (3:1). Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo. Purify by chromatography on silica gel (80 g) eluting with DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) (1:0 over 5 min, 19:1 over 5 min, 9:1 over 35 min, 85:15; 50 mL/min) to give the title compound (181 mg, 49%). MS (APCI+) m/z: 256 (M+H)+.

Workup

  1. temperatureto warm to room temperature
  2. stirringstir for 2 h
  3. custompartition between water and chloroform
  4. extractionExtract the aqueous phase three times with chloroform/iso-propanol (3:1)
  5. dry with materialDry the combined organic extracts over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify by chromatography on silica gel (80 g)
  9. washeluting with DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) (1:0 over 5 min, 19:1 over 5 min, 9:1 over 35 min, 85:15; 50 mL/min)

Sources & evidence

ORD record
ord-0592c4fcf4cb41de9c705ba28e1a909f
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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