2,2,2-Trifluoroethyl formate → HCID 11159516, compound

HRID 1700839Notes

Reaction equation

HRID 1700839 reaction equation
[C:1]1([C@@H:7]([NH:9][OH:10])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:11](OCC(F)(F)F)=[O:12]>O1CCCC1>[OH:10][N:9]([C@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:8])[CH:11]=[O:12]

Participants

4

Reactant 2

HCID 1416812,2,2-Trifluoroethyl formateHCID 10911281(S)-1-PHENYLETHYLHYDROXYLAMINE

Product 1

HCID 11159516HCID 11159516, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A solution of Example 2B (1.5 g, 10.95 mmol) in tetrahydrofuran (15 mL, 10 vols) was treated with the 2,2,2-trifluoroethyl formate reagent (92% wt, 7.6 g, 54.7 mmol, 5 equiv). The resulting mixture was heated at 65° C. for 18 hours and concentrated. The concentrate was distilled under vacuum (170° C. at 1.6 mm Hg) to provide 1.6 g (89%) of the desired product. 1H NMR (300 MHz, CDCl3) δ 8.00 (s, 1H), 7.54-7.30 (m, 5H), 4.93 (q, 1H, J=7 Hz), 1.82 (d, 3H, J=7 Hz).

Workup

  1. concentrationconcentrated
  2. distillationThe concentrate was distilled under vacuum (170° C. at 1.6 mm Hg)

Sources & evidence

ORD record
ord-fef84c69c96d428cb277eb4c46e9685d
Source dataset
uspto-grants-2002_02
Patent number
US06350902B2

Reaction notes

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