Lithium tri-s-butylborohydride → HCID 86640805, compound

HRID 2198221Notes

Reaction equation

HRID 2198221 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](/[C:8](=[N:11]/[S:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:13])/[CH2:9][CH3:10])[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:11][S:12]([C:14]([CH3:15])([CH3:17])[CH3:16])=[O:13])[CH2:9][CH3:10])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 87126783HCID 87126783, compound

Product 1

HCID 86640805HCID 86640805, 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)-prop-(E)-ylidene]-amide (6.0 g, 19 mmol) in THF (280 mL) was added a 1 M solution of L-Selectride in THF (37.8 ml, 37.8 mmol) dropwise. After 2.5 hours, the reaction 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 purifed by silica gel chromatography eluting with a gradient of 0-100% EtOAc in hexanes to afford an oily solid, which after further drying provided 2-methyl-propane-2-sulfinic acid [(R)-1-(2-bromo-pyridin-4-yl)-propyl]-amide as a crystalline solid.

Workup

  1. customthe reaction 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. washeluting with a gradient of 0-100% EtOAc in hexanes
  7. customto afford an oily solid, which
  8. customafter further drying

Sources & evidence

ORD record
ord-16e33034798d4e94b369ff551da3f49a
Source dataset
uspto-grants-2012_12
Patent number
US08338610B2

Reaction notes

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