Sodium borohydride → HCID 66958239, compound

HRID 1619112Notes

Reaction equation

HRID 1619112 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]3([CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]3)[C:9](=[O:13])[NH:10]2)=[CH:6][CH:5]=1>CO>[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]3([CH2:18][CH2:17][CH:16]([OH:19])[CH2:15][CH2:14]3)[C:9](=[O:13])[NH:10]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66953983HCID 66953983, compound

Product 1

HCID 66958239HCID 66958239, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (77 mg, 2.0 mmol) was added portionwise to a stirred suspension of 6′-bromospiro[cyclohexane-1,3′-indoline]-2′,4-dione (preparation 21a, 0.30 g, 1.0 mmol) in methanol (14 mL) at room temperature. After 2.5 hours the mixture was concentrated in vacuo and water was added. The mixture was extracted with ethyl acetate and the organic layer was dried (MgSO4) and evaporated to give the title compound as a mixture of isomers. Separation of the isomers was achieved by reverse phase chromatography (C-18 silica from Waters©, water/acetonitrile/methanol as eluents [0.1% v/v formic acid buffered] 0% to 60%) to give, in order of elution, the pure minor isomer as a white solid (0.075 g, 25%):

Workup

  1. concentrationAfter 2.5 hours the mixture was concentrated in vacuo and water
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-308695deada040a2b284b2d24e1c61bb
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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