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

HRID 1361168노트

반응식

HRID 1361168 반응식
[CH3:1][S:2]([C:5]1[O:9][C:8](/[C:10](=[N:13]/[S@@:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[O:15])/[CH2:11][CH3:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>C1COCC1>[CH3:1][S:2]([C:5]1[O:9][C:8]([C@@H:10]([NH:13][S@@:14]([C:16]([CH3:17])([CH3:19])[CH3:18])=[O:15])[CH2:11][CH3:12])=[CH:7][CH:6]=1)(=[O:3])=[O:4]

참가 물질

4

반응물 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 59278140(NE,R)-2-methyl-N-[1-(5-methylsulfonylfuran-2-yl)propylidene]propane-2-sulfinamide

생성물 1

HCID 59278508(R)-2-methyl-propane-2-sulfinic acid [(S)-1-(5-methanesulfonyl-furan-2-yl)-propyl]amide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a chilled (−78° C.) solution of (R)-2-methyl-propane-2-sulfinic acid[1-(5-methanesulfonyl-furan-2-yl)-prop-(E)-ylidene]-amide (0.360 g, 1.18 mmol) in THF (15 mL) was added a 1 M solution of L-Selectride (2.4 mL, 2.4 mmol) in THF in several portions. After stirring for 2 hours, the mixture was quenched with saturated aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated. The crude residue was purified by silica gel chromatography eluting with a gradient of 0-100% ethyl acetate in hexanes to afford (R)-2-methyl-propane-2-sulfinic acid [(S)-1-(5-methanesulfonyl-furan-2-yl)-propyl]-amide.

후처리

  1. customthe mixture was quenched with saturated aqueous ammonium chloride (100 mL)
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. washThe combined organic layers were washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by silica gel chromatography
  8. washeluting with a gradient of 0-100% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-953ece4043eb433192b7dfa3fccc2fe5
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879873B2

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