Sodium borohydride → HCID 70244802, compound

HRID 2269563Notes

Reaction equation

HRID 2269563 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:41])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]=[C:17]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[O:21][C:20]4[CH:28]=[CH:29][CH:30]=[C:31]([O:32][C:33]([C:36](OCC)=[O:37])([CH3:35])[CH3:34])[C:19]=4[CH2:18]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:41])[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH:16]=[C:17]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[O:21][C:20]4[CH:28]=[CH:29][CH:30]=[C:31]([O:32][C:33]([CH3:34])([CH3:35])[CH2:36][OH:37])[C:19]=4[CH2:18]3)[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66757871HCID 66757871, compound

Product 1

HCID 70244802HCID 70244802, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of product of example 138 (500 mg) in methanol (5 ml) was added sodium borohydride (330 mg), and the mixture was heated to reflux for 1 hour. The mixture was distilled off under reduced pressure. Water and ethyl acetate were added to the residue, the organic layer was separated and washed with saturated aqueous sodium chloride, and dried with magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography eluting with chloroform-methanol (10:1) to give the titled compound (440 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. distillationThe mixture was distilled off under reduced pressure
  4. additionWater and ethyl acetate were added to the residue
  5. customthe organic layer was separated
  6. washwashed with saturated aqueous sodium chloride
  7. dry with materialdried with magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by silica gel chromatography
  10. washeluting with chloroform-methanol (10:1)

Sources & evidence

ORD record
ord-eb9cab672a5443a9873bca4ee3689d87
Source dataset
uspto-grants-2001_12
Patent number
US06329385B1

Reaction notes

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