Sodium borohydride → N-[1-(1,3-benzothiazol-6-yl)ethyl]-2-methylpropane-2-sulfinamide

HRID 2108840ノート

反応式

HRID 2108840 の反応式
[S:1]1[C:5]2[CH:6]=[C:7]([C:10](=O)[CH3:11])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[CH3:13][C:14]([S@:17]([NH-:19])=[O:18])([CH3:16])[CH3:15].[BH4-].[Na+]>[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC.C1COCC1>[S:1]1[C:5]2[CH:6]=[C:7]([CH:10]([NH:19][S:17]([C:14]([CH3:16])([CH3:15])[CH3:13])=[O:18])[CH3:11])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

参加物

6

反応物 3

HCID 4311764Sodium borohydrideHCID 108211871-(1,3-Benzothiazol-6-yl)ethan-1-oneHCID 86609349(R)-t-butylsulfinylamide

生成物 1

HCID 68843346N-[1-(1,3-benzothiazol-6-yl)ethyl]-2-methylpropane-2-sulfinamide

試薬・触媒・溶媒 2

HCID 76524Titanium tetraethoxide触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
85 °C

実験手順

To a THF (6 ml) solution of 1-(1,3-benzothiazol-6-yl)ethanone (European Journal of Organic Chemistry (1998), (9), 2047-2050., 250 mg, 1.41 mmol) and (R)-(+)-2-methyl-2-propane sulfinylamide (188 mg, 1.55 mmol), titanium(IV) ethoxide (2 ml) was added and the mixture was stirred for 40 minutes at 85° C. under microwave condition. The mixture was then cooled to 0° C. and sodium borohydride (188 mg, 5.0 mmol) was added to the reaction mixture. After stirring for 2 hours at the temperature, the reaction was partitioned with water and EtOH followed by stirring for 1 hour at room temperature. Then, filtration, evaporation gave N-[1-(1,3-benzothiazol-6-yl)ethyl]-2-methylpropane-2-sulfinamide (MS (ESI) m/z 281 (M−H)−, 283 (M+H)+) which was then added hydrochloric acid-MeOH (2.0 M, 7.0 ml) and 1,4-dioxane (7.0 ml). The mixture was then stirred for 1.5 hours at room temperature and the same reaction procedure as Example 14 was performed to give the title compound. MS (ESI) m/z 180 (M−H)+

後処理

  1. temperatureThe mixture was then cooled to 0° C.
  2. stirringAfter stirring for 2 hours at the temperature
  3. customthe reaction was partitioned with water and EtOH
  4. stirringby stirring for 1 hour at room temperature
  5. filtrationThen, filtration, evaporation

出典と根拠

ORDレコード
ord-bdf259c3edc845d2bce40ff1f8583d7a
出典データセット
uspto-grants-2009_04
特許番号
US07514457B2

反応ノート

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