Water → (S)-1-(6-iodobenzo[d]thiazol-2-yl)pyrrolidin-3-ol

HRID 2040958ノート

反応式

HRID 2040958 の反応式
[I:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]=[C:7](S(C)(=O)=O)[S:8][C:4]=2[CH:3]=1.[NH:15]1[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[I:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]=[C:7]([N:15]3[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16]3)[S:8][C:4]=2[CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2733874(3S)-pyrrolidin-3-olHCID 669061396-Iodo-2-(methylsulfonyl)benzo[d]thiazole

生成物 1

HCID 66905790(S)-1-(6-iodobenzo[d]thiazol-2-yl)pyrrolidin-3-ol

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

A stirred mixture of 6-iodo-2-(methylsulfonyl)benzo[d]thiazole (Reference Example 6c, 1.50 g, 4.42 mmol), (S)-pyrrolidin-3-ol (0.500 g, 5.74 mmol), and potassium carbonate (1.222 g, 8.84 mmol) in N,N-dimethylformamide (21.5 mL) was heated to 150° C. under microwave irradiation for 10 minutes. The reaction mixture was cooled to room temperature, then poured into water (350 mL) to give a precipitate. The precipitate was collected by filtration, rinsed with water, and then dissolved in ethyl acetate. The ethyl acetate solution was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to give a crude solid that was purified by silica gel chromatography (100% CHCl3 to 97:3 CHCl3/methanol). Fractions containing product were combined an concentrated under reduced pressure to provide (S)-1-(6-iodobenzo[d]thiazol-2-yl)pyrrolidin-3-ol. 1H NMR (300 MHz, CD3OD) δ ppm 2.03-2.14 (m, 1H), 2.15-2.29 (m, 1H), 3.47-3.55 (m, 1H), 3.58-3.75 (m, 3H), 4.53-4.59 (m, 1H), 7.23 (d, J=8 Hz, 1H), 7.53-7.59 (m, 1H), 7.95-7.98 (m, 1H); MS (DCI/NH3) m/z 347 (M+H)+.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customto give a precipitate
  3. filtrationThe precipitate was collected by filtration
  4. washrinsed with water
  5. dissolutiondissolved in ethyl acetate
  6. dry with materialThe ethyl acetate solution was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customto give a crude solid that
  10. customwas purified by silica gel chromatography (100% CHCl3 to 97:3 CHCl3/methanol)
  11. additionFractions containing product
  12. concentrationan concentrated under reduced pressure

出典と根拠

ORDレコード
ord-ab0797c16f3145c5bf68283efdd06899
出典データセット
uspto-grants-2013_11
特許番号
US08580968B2

反応ノート

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