Tetrahydrofuran → 3-Hydroxymethyl-2-(4-methoxyphenylmethyl)-2H-thieno[3,2-e]-1,2-thiazine-3-methanol 1,1-dioxide

HRID 1736013노트

반응식

HRID 1736013 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[C:15]([C:16](OCC)=[O:17])=[CH:14][C:13]3[CH:21]=[CH:22][S:23][C:12]=3[S:11]2(=[O:25])=[O:24])=[CH:5][CH:4]=1.CC(C[AlH]CC(C)C)C.C1C[O:38][CH2:37]C1>>[OH:38][CH2:37][C:15]1([CH2:16][OH:17])[CH2:14][C:13]2[CH:21]=[CH:22][S:23][C:12]=2[S:11](=[O:24])(=[O:25])[N:10]1[CH2:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1

참가 물질

4

반응물 3

HCID 8028TetrahydrofuranHCID 14487Diisobutylaluminum hydride2회HCID 19434025Ethyl 2-(4-methoxyphenylmethyl)-2H-thieno[3,2-e]-1,2-thiazine-3-carboxylate 1,1-dioxide

생성물 1

HCID 677348383-Hydroxymethyl-2-(4-methoxyphenylmethyl)-2H-thieno[3,2-e]-1,2-thiazine-3-methanol 1,1-dioxide

실험 절차

To a solution of the product from Step B (1.80 g, 4.75 mmol) in anhydrous THF (40 mL) at ambient temperature was added DIBAL (1.0M, 11.87 mL, 11.87 mmol) and the mixture was stirred for 1 h. Additional DIBAL (1M, 15 mL,15 mmol) was added (TLC showed starting material remained) and the reaction mixture was stirred for 20 h, cooled (ice bath) and the reaction was quenched by the slow addition of 1N HCl (100 mL). THF was evaporated and the aqueous mixture was extracted with ethyl acetate (2×100 mL). The combined extracts were dried (MgSO4), filtered and evaporated to give an oil (1.60 g) which was used in the next step without further purification.

후처리

  1. stirringthe reaction mixture was stirred for 20 h
  2. temperaturecooled (ice bath)
  3. customthe reaction was quenched by the slow addition of 1N HCl (100 mL)
  4. customTHF was evaporated
  5. extractionthe aqueous mixture was extracted with ethyl acetate (2×100 mL)
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

출처 및 근거

ORD 기록
ord-7498f9ebe14d4d3f8bcc298920919814
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05538966

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