Diisopropylethylamine → (2S)-2-((S)-Phenyl{[2-(trifluoromethyl)phenyl]thio}methyl)morpholine

HRID 131188Notes

Reaction equation

HRID 131188 reaction equation
CCN(C(C)C)C(C)C.C1([C@H]([N:18]2[CH2:23][CH2:22][O:21][C@H:20]([C@H:24]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[S:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:35])([F:34])[F:33])[CH2:19]2)C)C=CC=CC=1.ClC(OC(Cl)C)=O>ClCCl>[C:36]1([C@H:24]([S:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]([F:33])([F:34])[F:35])[C@H:20]2[O:21][CH2:22][CH2:23][NH:18][CH2:19]2)[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5213051-Chloroethyl chloroformateHCID 69313855(2S)-4-[(1R)-1-Phenylethyl]-2-((S)-phenyl{[2-(trifluoromethyl)phenyl]thio}methyl)morpholine

Product 1

HCID 9798640(2S)-2-((S)-Phenyl{[2-(trifluoromethyl)phenyl]thio}methyl)morpholineYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of polymer supported Hünig's base (0.11 g, 0.40 mmol) and 52 (0.03 g, 0.066 mmol) in dry dichloromethane (1 ml) was added α-chloroethyl chloroformate (0.09 g, 0.066 mmol) at room temperature under nitrogen. The mixture was stirred at room temperature over the weekend then filtered and concentrated in vacuo. This was taken up in methanol, heated at 70° C. for 2 hours, cooled, and purified by SCX chromatography (eluent: ammonia/methanol 1/1 [v/v]) to give 9 as a colourless oil (0.01 g, 43%). The spectroscopic data for 9 obtained by the route outlined here was identical to the data for 9 obtained as described above.

Workup

  1. additionTo a suspension of polymer
  2. filtrationthen filtered
  3. concentrationconcentrated in vacuo
  4. temperatureheated at 70° C. for 2 hours
  5. temperaturecooled
  6. custompurified by SCX chromatography (eluent: ammonia/methanol 1/1 [v/v])

Sources & evidence

ORD record
ord-7286a69d8ed54bc0817bc7af3e86eca9
Source dataset
uspto-grants-2008_06
Patent number
US07384941B2

Reaction notes

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