Lithium tri-s-butylborohydride → 2-methyl-propane-2-sulfinic acid [(S)-1-(2-methanesulfonyl-thiazol-5-yl)-propyl]amide

HRID 559691Notes

Reaction equation

HRID 559691 reaction equation
[CH3:1][S:2]([C:5]1[S:6][C:7](/[C:10](=[N:13]\[S:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[O:15])/[CH2:11][CH3:12])=[CH:8][N:9]=1)(=[O:4])=[O:3].C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+]>C1COCC1>[CH3:1][S:2]([C:5]1[S:6][C:7]([C@@H:10]([NH:13][S:14]([C:16]([CH3:17])([CH3:19])[CH3:18])=[O:15])[CH2:11][CH3:12])=[CH:8][N:9]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 87126692(NZ)-2-methyl-N-[1-(2-methylsulfonyl-1,3-thiazol-5-yl)propylidene]propane-2-sulfinamide

Product 1

HCID 667274522-methyl-propane-2-sulfinic acid [(S)-1-(2-methanesulfonyl-thiazol-5-yl)-propyl]amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a chilled (−78° C.) solution of 2-methyl-propane-2-sulfinic acid [1-(2-methanesulfonyl-thiazol-5-yl)-prop-(Z)-ylidene]-amide (93 mg, 0.29 mmol) in THF (5 mL) was added a 1 M solution of lithium tri-sec-butylborohydride (L-Selectride) (0.58 mL, 0.58 mmol) in THF dropwise. After 2.5 hours, the reaction mixture was quenched with saturated aqueous ammonium chloride solution (100 mL), and the aqueous layer was separated. The aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 0-100% ethyl acetate in hexanes to afford 2-methyl-propane-2-sulfinic acid [(S)-1-(2-methanesulfonyl-thiazol-5-yl)-propyl]-amide.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous ammonium chloride solution (100 mL)
  2. customthe aqueous layer was separated
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×10 mL)
  4. washThe combined organic layers were washed with brine (10 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with a gradient of 0-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-766e97456328416697d661e2779d1313
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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