(Diethylamino)sulfur trifluoride → 1-[2-(2,4-Difluorophenyl)-2-fluoroethyl]-3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine

HRID 10220

反応式

HRID 10220 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9](O)[CH2:10][N:11]1[CH2:14][CH:13]([CH2:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:12]1.C(N(S(F)(F)[F:33])CC)C>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([F:33])[CH2:10][N:11]1[CH2:14][CH:13]([CH2:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:12]1

参加物

4

反応物 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 219783771-(2,4-Difluorophenyl)-2-(3-{[(4-fluorophenyl)sulfonyl]methyl}azetidin-1-yl)ethanol

生成物 1

HCID 219783951-[2-(2,4-Difluorophenyl)-2-fluoroethyl]-3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine収率 50.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A stirred suspension of the alcohol from Step 1 (130 mg, 0.33 mmol) in dichloromethane (4 mL) under nitrogen was cooled to −10° C. (Diethylamino)sulfur trifluoride (54 μL, 0.41 mmol) was added dropwise and after 30 minutes the cooling bath was removed. After a further 15 minutes, the reaction was quenched with saturated aqueous sodium hydrogencarbonate solution and extracted with dichloromethane. The combined organic layers were washed with water and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by preparative TLC (50% ethyl acetate/isohexane) to give the title compound (64 mg, 50%). 1H NMR (500 MHz, CDCl3) δ 7.91–7.89 (2H, m), 7.40–7.34 (1H, m), 7.27–7.23 (2H, m), 6.90 (1H, t, J=8.2 Hz), 6.79 (1H, t, J=9.5 Hz), 5.70–5.58 (1H, m), 3.49 (2H, q, J=7.4 Hz), 3.38–3.36 (2H, m), 2.95 (2H, q, J=6.7 Hz), 2.90–2.70 (3H, m); m/z (ES+) 388 (M+H)+.

後処理

  1. additionwas added dropwise and after 30 minutes the cooling bath
  2. customwas removed
  3. customthe reaction was quenched with saturated aqueous sodium hydrogencarbonate solution
  4. extractionextracted with dichloromethane
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo
  8. customThe residue was purified by preparative TLC (50% ethyl acetate/isohexane)

出典と根拠

ORDレコード
ord-b174bf58a91345e78452294c1af287b0
出典データセット
uspto-grants-2006_08
特許番号
US07094777B2

関連ノート

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