Sodium borohydride → HCID 20190714, compound

HRID 1759244Notes

Reaction equation

HRID 1759244 reaction equation
[C:1]1([N:7]=[C:8]2[CH2:17][CH2:16][N:15]3[CH:10]([CH2:11][CH2:12][CH:13]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH2:14]3)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].CCOC(C)=O.CC(C)=O>CO>[NH:7]([CH:8]1[CH2:17][CH2:16][N:15]2[CH:10]([CH2:11][CH2:12][CH:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:14]2)[CH2:9]1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 13034467HCID 13034467, compoundHCID 21584569Ethylacetate acetone

Product 1

HCID 20190714HCID 20190714, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude anil (IV) (7.2 g.) was dissolved in MeOH (100 ml.), cooled in an ice bath and then NaBH4 (3.6 g.) added portionwise. The mixture was refluxed for 1 hr. and cooled. The solvent was removed and the residue treated with EtOAc/H2O. The EtOAc extracts were combined, dried over MgSO4 and solvent removed in vacuo. Yield, 6.7 g. The TLC showed two spots (most likely two isomers). The mixture was run through a HPLC using EtOAc/acetone (5:1). The mixture was not easily separated and the main portion (4 g.) was still a mixture. The mixture was carried through the rest of the synthesis. Also obtained was the fast component pure (0.7 g.) and the slow component pure (0.4 g.)

Workup

  1. temperaturecooled in an ice bath
  2. temperatureThe mixture was refluxed for 1 hr
  3. temperatureand cooled
  4. customThe solvent was removed
  5. additionthe residue treated with EtOAc/H2O
  6. dry with materialdried over MgSO4 and solvent
  7. customremoved in vacuo
  8. customYield
  9. customThe mixture was not easily separated
  10. customThe mixture was carried through the rest of the synthesis
  11. customAlso obtained

Sources & evidence

ORD record
ord-5b190080b5bd4fdfa7f2ef29a1f48cdd
Source dataset
uspto-grants-1982_07
Patent number
US04339582

Reaction notes

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