Lithium tri-s-butylborohydride → HCID 86640807, compound

HRID 559761Notes

Reaction equation

HRID 559761 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-bromo-pyridin-4-yl)-eth-(E)-ylidene]-amide (9.3 g, 31 mmol) in THF (280 mL) was added a 1 M solution of L-Selectride in THF (61.3 ml, 61.3 mmol) dropwise. After 2.5 hours, the chilled mixture was quenched with saturated aqueous NH4Cl (100 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×400 mL). The combined organic layers were washed with brine, and concentrated. The residue was 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-bromo-pyridin-4-yl)-ethyl]-amide as a light yellow oil which contained 5% of the opposite diastereomer.

Workup

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

Sources & evidence

ORD record
ord-9dab7f19e9fe4885b1a97c1ccf2d08be
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

Loading…