Triethylamine → N1-(2-Hydroxy-3,3,3-trifluoro-1-isopropylpropyl) N2-phenylmethyloxycarbonyl-prolinamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1.1 g of N-phenylmethyloxycarbonyl proline TDO-ester (Cf Hollitzer, Seewald and Steglichm Ang.Int. Edit. 1976, Vol. 15, 444) and 0.42 g of 3-amino-1,1,1-trifluoro-4-methyl-2-pentanol hydrochloride in 50 ml of CH2Cl2 was added dropwise 0.40 g of triethylamine. After stirring for 14 hours at 25° C., aqueous KHSO4 was added, the layers separated and the organic layer washed with aqueous KHSO4, aqueous KHCO3, H2O and then brine (2×). After drying (MgSO4), solvents were flash evaporated to yield 0.54 g of a solid residue which was recrystallized in Et2O to give 0.24 g of the analytically pure expected amide; m.p. 99° C.

Provenance & Evidence