Diisopropylethylamine → HCID 117871962, compound

HRID 530604Notes

Reaction equation

HRID 530604 reaction equation
Cl.[F:2][C:3]([F:17])([F:16])[C:4]1[CH:5]=[C:6]([CH:10]2[O:15][CH2:14][CH2:13][NH:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1.CCN(C(C)C)C(C)C.[F:27][C:28]([F:33])([F:32])[C@@H:29]1[CH2:31][O:30]1>C(#N)C>[F:27][C:28]([F:33])([F:32])[C@@H:29]([OH:30])[CH2:31][N:12]1[CH2:13][CH2:14][O:15][CH:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([C:3]([F:2])([F:16])[F:17])[CH:5]=2)[CH2:11]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2080462-(3-(Trifluoromethyl)phenyl)morpholine hydrochlorideHCID 7171781(2S)-2-(Trifluoromethyl)oxirane

Product 1

HCID 117871962HCID 117871962, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a 50 mL round-bottomed flask, 2-(3-(trifluoromethyl)phenyl)morpholine hydrochloride (515 mg, 1.92 mmol) and DIPEA (249 mg, 336 μl, 1.92 mmol) were combined with acetonitrile (10 ml) to give a white suspension. (S)-2-(trifluoromethyl)oxirane (323 mg, 2.89 mmol) was added. The reaction mixture was stirred at room temperature for 3 days and then was concentrated in vacuo. The reaction mixture was taken up in 100 mL dilute aqueous NaHCO3 and extracted with dichloromethane (3×50 mL). The organic layers were dried over Na2SO4 and concentrated in vacuo to afford 528 mg (80%) of (2S)-1,1,1-trifluoro-3-(2-(3-(trifluoromethyl)phenyl)morpholino)propan-2-ol, which was used as is in the next step. (M+H)+=344 m/e.

Workup

  1. customto give a white suspension
  2. concentrationwas concentrated in vacuo
  3. extractionextracted with dichloromethane (3×50 mL)
  4. dry with materialThe organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-750037e53ccd4a8fa6396ea4c3d182b0
Source dataset
uspto-grants-2016_05
Patent number
US09353096B2

Reaction notes

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