Lithium borohydride → HCID 22711069, compound

HRID 352882Notes

Reaction equation

HRID 352882 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[N:18]([S:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)(=[O:29])=[O:28])[C:19]3[C:24]([CH:25]=2)=[CH:23][C:22]([Cl:26])=[CH:21][CH:20]=3)(=[O:16])=[O:15])[CH2:10][CH:9]1[CH2:36][C:37](OC)=[O:38])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+]>O1CCCC1CO>[Cl:26][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[N:18]([S:27]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)(=[O:29])=[O:28])[C:17]([S:14]([N:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:9]([CH2:36][CH2:37][OH:38])[CH2:10]1)(=[O:15])=[O:16])=[CH:25]2

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 22710254HCID 22710254, compound

Product 1

HCID 22711069HCID 22711069, compound

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

In tetrahydrofuran - methanol (10/1, 55 mL) was dissolved 4-(tert-butoxycarbonyl)-1-[(5-chloro-1-phenylsulfonylindol-2-yl)sulfonyl]-3-[(methoxycarbonyl)methyl]piperazine (2.5 g), followed by the addition of lithium borohydride (135 mg). The resulting mixture was stirred for 48 hours. The solvent was distilled off under reduced pressure. Water and chloroform were then added to the reaction mixture and the mixture was separated into layers. The organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue was subjected to chromatography on a silica gel column (ethyl acetate:hexane=2:3), whereby the title compound (1.84 g) was obtained as a colorless oil.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionWater and chloroform were then added to the reaction mixture
  3. customthe mixture was separated into layers
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customwas obtained as a colorless oil

Sources & evidence

ORD record
ord-a7ed827c6ca042ab8d5458f5a52bbff8
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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