Sodium borohydride → HCID 57535417, compound

HRID 1455659Notes

Reaction equation

HRID 1455659 reaction equation
[CH3:1][C:2]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([C:24]4[C:25]([C:32]5[CH:37]=[CH:36][C:35]([S:38][CH3:39])=[CH:34][CH:33]=5)=[CH:26][C:27]([CH:30]=[O:31])=[CH:28][CH:29]=4)[CH:21]=[CH:22][CH:23]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([S:4]([CH3:7])(=[O:6])=[O:5])[CH3:3].[BH4-].[Na+]>CCO.C1COCC1>[CH3:3][C:2]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([C:24]4[C:25]([C:32]5[CH:33]=[CH:34][C:35]([S:38][CH3:39])=[CH:36][CH:37]=5)=[CH:26][C:27]([CH2:30][OH:31])=[CH:28][CH:29]=4)[CH:21]=[CH:22][CH:23]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([S:4]([CH3:7])(=[O:5])=[O:6])[CH3:1]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86608356HCID 86608356, compound

Product 1

HCID 57535417HCID 57535417, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of aldehyde from step 2 in EtOH: THF (4:1, 0.05M) at 0° C. was added NaBH4 (1 eq). The reaction mixture was stirred 1 h at 0° C., quenched with a solution of NH4Cl and diluted with ether. The organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (hexane:EtOAc, 1:1 to 1:9) to afforded the title compound.

Workup

  1. customquenched with a solution of NH4Cl
  2. additiondiluted with ether
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (hexane:EtOAc, 1:1 to 1:9)

Sources & evidence

ORD record
ord-1c51d3971d344dc2a89aad2f7e8f79e9
Source dataset
uspto-grants-2009_01
Patent number
US07482456B2

Reaction notes

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