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

HRID 131187Notes

Reaction equation

HRID 131187 reaction equation
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

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 27778892-(Trifluoromethyl)benzenethiolHCID 59732174HCID 59732174, compound

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5515106e8c7d43c79231da658baddb5e
Source dataset
uspto-grants-2008_06
Patent number
US07384941B2

Reaction notes

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