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

HRID 1736013ノート

反応式

HRID 1736013 の反応式
[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

参加物

4

反応物 3

HCID 8028TetrahydrofuranHCID 14487Diisobutylaluminum hydride2 回HCID 19434025Ethyl 2-(4-methoxyphenylmethyl)-2H-thieno[3,2-e]-1,2-thiazine-3-carboxylate 1,1-dioxide

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7498f9ebe14d4d3f8bcc298920919814
出典データセット
uspto-grants-1996_07
特許番号
US05538966

反応ノート

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