Ethanolamine → Oxazolidine, 2-methyl-2-(trifluoromethyl)-

HRID 2169181Notes

Reaction equation

HRID 2169181 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].[F:5][C:6]([F:11])([F:10])[C:7](=O)[CH3:8]>ClCCl>[CH3:8][C:7]1([C:6]([F:11])([F:10])[F:5])[NH:1][CH2:2][CH2:3][O:4]1

Participants

4

Conditions

Temperature
-30 °C

Procedure

A solution of 2-aminoethanol (10.15 g, 10.0 ml, 166 mmol, Eq: 1.00) in dichloromethane (250 ml) was cooled to −30° C. and stirred while 1,1,1-trifluoropropan-2-one (20.1 g, 16.1 ml, 179 mmol, Eq: 1.08), followed by molecular sieves (4 Å, powder <5 micron, activated; 20.0 g, 166 mmol, Eq: 1.00) were added. The mixture was stirred at −30° C. for 3 h and then allowed to warm to room temperature and left stirring for overnight. The mixture was filtered, washed with dichloromethane, and concentrated to obtain 2-methyl-2-(trifluoromethyl)oxazolidine (39) (oil, 15.60 g, 101 mmol, 60.5% yield).

Workup

  1. additionwere added
  2. temperatureto warm to room temperature
  3. waitleft
  4. stirringstirring for overnight
  5. filtrationThe mixture was filtered
  6. washwashed with dichloromethane
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f0181f17c1d0418ca29c1159c57a4a8e
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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