Lithium tri-s-butylborohydride → HCID 86640807, compound

HRID 1423053Notes

Reaction equation

HRID 1423053 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](/[C:8](=[N:10]/[S:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[O:12])/[CH3:9])[CH:5]=[CH:4][N:3]=1.CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([C@@H:8]([NH:10][S:11]([C:13]([CH3:14])([CH3:16])[CH3:15])=[O:12])[CH3:9])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 87126742HCID 87126742, compound

Product 1

HCID 86640807HCID 86640807, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a chilled (−78° C.) solution of 2-methyl-propane-2-sulfinic acid [1-(2-bromopyridin-4-yl)-eth-(E)-ylidene]-amide (9.3 g, 31 mmol) in THF (280 mL) is added a 1 M solution of L-Selectride in THF (61.3 mL, 61.3 mmol) dropwise. After 2.5 hours, the chilled mixture is quenched with saturated aqueous NH4Cl (100 mL). The layers are separated and the aqueous layer is extracted with EtOAc (2×400 mL). The combined organic layers are washed with brine, and concentrated. The residue is purified by silica gel chromatography eluting with a gradient of 50-90% EtOAc in hexanes to afford 2-methyl-propane-2-sulfinic acid [(S)-1-(2-bromopyridin-4-yl)-ethyl]-amide as an oil which contained 5% of the opposite diastereomer.

Workup

  1. customthe chilled mixture is quenched with saturated aqueous NH4Cl (100 mL)
  2. customThe layers are separated
  3. extractionthe aqueous layer is extracted with EtOAc (2×400 mL)
  4. washThe combined organic layers are washed with brine
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel chromatography
  7. washeluting with a gradient of 50-90% EtOAc in hexanes

Sources & evidence

ORD record
ord-f90fe03b15e343fbaf6739782597d5c8
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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