Triethylamine → HCID 10108338, compound

Participants

Reaction Conditions

Reaction Steps

(R)-3-(N-Isopropyl,N-n-propylamino)-5-trifluoromethanesulfonyloxychroman (4.0 g, 10.5 mmol), triethylamine (2.3 g, 23.1 mmol) and a mixture of DMF/MeOH (18 mL, 6:2) was mixed in a three necked round-bottom flask. The flask was evacuated followed by inlet of CO-gas (repeated two times). Finally 1,3-bis(diphenylphosfino)propane (0.11 g, catalytic amount) and palladium(II)acetate (0.07 g, catalytic amount)) was added before the mixture was stirred at 70° C. for 17 hours. The recation mixture was diluted with diethyl ether, washed with 2M NH3 and dried (MgSO4). Removal of solvent in vacuo gave a brown oily residue which was purified by flash chromatography (SiO2, CH2Cl2 /EtOAc; 10:1) to give the title compound in 82% yield (2.5 g). [α]D21 -131.6° (MeOH 0.1M, 21° C.). Mp 125.5°-127.4° C. Anal. Calcd for C17H26O3NCl: C, 62.3; H, 8.0; N, 4.3. Found: C, 62.5; H, 7.9; N, 4.4.

Provenance & Evidence