Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate → methyl 3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate

HRID 641325ノート

反応式

HRID 641325 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[S:13][CH2:12][C:11](=O)[NH:10][C:9]=2[CH:15]=1)=[O:4]>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[S:13][CH2:12][CH2:11][NH:10][C:9]=2[CH:15]=1)=[O:4]

参加物

3

反応物 1

HCID 699501Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate

生成物 1

HCID 17796647methyl 3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate収率 96%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Borane-tetrahydrofuran complex solution (1 M in tetrahydrofuran, 45 mL, 45 mmol) was added at 0° C. to a suspension of methyl-3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate (2.00 g, 8.96 mmol) in tetrahydrofuran (20 mL). The ice bath was removed, the homogenous solution stirred at room temperature for 2 h, then excess reagent was destroyed by careful addition of methanol (42 mL) at 0° C. After evaporation of volatile material, the residue was taken up in 5% methanolic sulfuric acid solution (25 mL) and the solution was heated at reflux over 80 min. After cooling, the reaction mixture was partitioned between ethyl acetate and water, the organic layer was dried (MgSO4) and evaporated to produce 3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid methyl ester (1.79 g, 96%). Light yellow solid, MS (ISP)=210.1 (M+H)+.

後処理

  1. customThe ice bath was removed
  2. customexcess reagent was destroyed by careful addition of methanol (42 mL) at 0° C
  3. customAfter evaporation of volatile material
  4. temperaturethe solution was heated
  5. temperatureat reflux over 80 min
  6. temperatureAfter cooling
  7. customthe reaction mixture was partitioned between ethyl acetate and water
  8. dry with materialthe organic layer was dried (MgSO4)
  9. customevaporated

出典と根拠

ORDレコード
ord-174708bb10dc4ea984c2b8663f64ef1a
出典データセット
uspto-grants-2010_04
特許番号
US07696200B2

反応ノート

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