Lithium tri-s-butylborohydride → HCID 86640805, compound

HRID 1423046Notes

Reaction equation

HRID 1423046 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-bromopyridin-4-yl)-prop-(E)-ylidene]-amide (6.0 g, 19 mmol) in THF (280 mL) is added a 1 M solution of L-Selectride in THF (37.8 mL, 37.8 mmol) dropwise. After 2.5 hours, the reaction 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 0-100% EtOAc in hexanes to afford an oily solid, which after further drying gives 2-methyl-propane-2-sulfinic acid [(R)-1-(2-bromopyridin-4-yl)-propyl]-amide as a crystalline solid.

Workup

  1. customthe reaction 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 0-100% EtOAc in hexanes
  8. customto afford an oily solid, which
  9. customafter further drying

Sources & evidence

ORD record
ord-0ce2f68f63d64744b9424d9383e6242f
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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