Water → HCID 131721737, compound

HRID 1637277Notes

Reaction equation

HRID 1637277 reaction equation
[C:1]([CH:7]1[CH2:12][CH2:11][N:10]([CH:13]2[C:23]3[C:24]4[C:16](=[C:17]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[NH:18][C:19]=4[CH:20]=[CH:21][CH:22]=3)[CH2:15][CH2:14]2)[CH2:9][CH2:8]1)([C:3](OC)=[O:4])=[O:2].[BH4-].[Li+].O>O1CCCC1>[OH:4][CH2:3][C:1]([CH:7]1[CH2:8][CH2:9][N:10]([CH:13]2[C:23]3[C:24]4[C:16](=[C:17]([C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=5)[NH:18][C:19]=4[CH:20]=[CH:21][CH:22]=3)[CH2:15][CH2:14]2)[CH2:11][CH2:12]1)=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydride2×HCID 131721736HCID 131721736, compound

Product 1

HCID 131721737HCID 131721737, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of the compound (100 mg) obtained in Example 157 in anhydrous tetrahydrofuran (THF; 20 ml) was added lithium borohydride (5.5 mg) under cooling with ice. The mixture was stirred for 5 minutes. After adding another lithium borohydride (5.5 mg), the mixture was stirred for further 5 minutes. Water was added to the reaction mixture, followed by extraction with methylene chloride. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/methylene chloride=1:1) to yield 45 mg (48%) of the titled compound.

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred for further 5 minutes
  3. extractionfollowed by extraction with methylene chloride
  4. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/methylene chloride=1:1)

Sources & evidence

ORD record
ord-edc979f4063847bcb5279232fd2a0d11
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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