tert-Butylsulfinamide, (S)-(-)- → (S)-2-Methyl-propane-2-sulfinic Acid ((3S)-1,3-dimethyl-pentylidene)-amide

HRID 132624

반응식

HRID 132624 반응식
[CH3:1][C@@H:2]([CH2:7][CH3:8])[CH2:3][C:4](=O)[CH3:5].[CH3:9][C:10]([S@@:13]([NH2:15])=[O:14])([CH3:12])[CH3:11]>C1COCC1.[Cl-].[Na+].O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[CH3:5][C:4](=[N:15][S@:13]([C:10]([CH3:12])([CH3:11])[CH3:9])=[O:14])[CH2:3][C@@H:2]([CH3:1])[CH2:7][CH3:8]

참가 물질

6

반응물 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 12208763(S)-4-methyl-hexan-2-one

생성물 1

HCID 86597956(S)-2-Methyl-propane-2-sulfinic Acid ((3S)-1,3-dimethyl-pentylidene)-amide수율 63.4%

시약·촉매·용매 3

HCID 76524Titanium tetraethoxide촉매HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

A mixture of (S)-4-methyl-hexan-2-one (1.6 g, 14 mmol), (S)-2-methyl-propane-2-sulfinic acid amide (1.7 g, 14 mmol) and titanium(IV) ethoxide (6.4 g, 28 mmol) in THF (30 mL) was refluxed for 10 hours. Then the reaction mixture was poured into brine (150 mL). The mixture was filtered. The filtrate was extracted by EtOAc (3×70 mL). The EtOAc phase was removed under reduce pressure and the residue was purified by a silica gel column (Hexane/EtOAc 3:1) to give the titled compound (1.93 g, 63% yield) as a colorless oil: 1H NMR (CDCl3) δ 2.24 (m, 2H), 2.27 (s, 3H), 1.85 (m, 1H), 1.22 (m, 2H), 1.20 (s, 9H), 0.85 (m, 6H); MS (APCI) (M+1)+ 218.1.

후처리

  1. temperaturewas refluxed for 10 hours
  2. filtrationThe mixture was filtered
  3. extractionThe filtrate was extracted by EtOAc (3×70 mL)
  4. customThe EtOAc phase was removed
  5. customthe residue was purified by a silica gel column (Hexane/EtOAc 3:1)

출처 및 근거

ORD 기록
ord-b893801a673040d08b755176e997b607
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07388023B2

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