Potassium Carbonate → (2S)-4-[(1R)-1-Phenylethyl]-2-((S)-phenyl{[2-(trifluoromethyl)phenyl]thio}methyl)morpholine

HRID 131187ノート

反応式

HRID 131187 の反応式
CS(O[C@H:6]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C@H:7]1[O:12][CH2:11][CH2:10][N:9]([C@@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:14])[CH2:8]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[F:33][C:34]([F:43])([F:42])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[SH:41]>>[C:15]1([C@H:13]([N:9]2[CH2:10][CH2:11][O:12][C@H:7]([C@H:6]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[S:41][C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=3[C:34]([F:33])([F:42])[F:43])[CH2:8]2)[CH3:14])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

参加物

4

反応物 3

HCID 11430Potassium CarbonateHCID 27778892-(Trifluoromethyl)benzenethiolHCID 59732174HCID 59732174、化合物

生成物 1

HCID 69313855(2S)-4-[(1R)-1-Phenylethyl]-2-((S)-phenyl{[2-(trifluoromethyl)phenyl]thio}methyl)morpholine収率 71%

実験手順

A mixture of 51 (0.035 g, 0.093 mmol), potassium carbonate (0.026 g, 0.19 mmol) and 2-trifluoromethylbenzenethiol (0.084 g, 0.47 mmol) in dry, degassed dimethylformamide (0.5 ml) was stirred under nitrogen at room temperature for 3 days. The reaction mixture was diluted with water and extracted with diethyl ether. The extracts was washed with water and brine, dried over magnesium sulphate, filtered and evaporated to give a colourless oil (0.03 g, 71%). Purification by flash column chromatography (eluent: ethyl acetate/heptane 20/80 [v/v]) gave 52 as a colourless oil (0.03 g, 71%); MW 457.56; C26H26F3NOS 1H NMR (CDCl3) 7.53 (1H, d), 7.10-7.28 (13H, m), 4.39 (1H, d), 3.85-4.04 (2H, m), 3.8 (1H, td), 3.35 (1H, q), 2.70 (1H, d), 2.40 (1H, d), 2.30 (1H, td), 2.10-2.20 (1H, m), 1.29 (3H, d). m/z [M+H]+ 458.

後処理

  1. customin dry
  2. customdegassed dimethylformamide (0.5 ml)
  3. additionThe reaction mixture was diluted with water
  4. extractionextracted with diethyl ether
  5. washThe extracts was washed with water and brine
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-5515106e8c7d43c79231da658baddb5e
出典データセット
uspto-grants-2008_06
特許番号
US07384941B2

反応ノート

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