Methyl iodide → HCID 18454787, compound

Participants

Reaction Conditions

Reaction Steps

Tetrahydrofuran (520 ml) and pyrrolidine (90 ml) are mixed and the mixture is cooled to −40° C. n-Butyl lithium in hexane (1.6M, 510 ml) is added under nitrogen atmosphere for 2 hours at −40° C. to −50° C. The contents are stirred for 30 minutes at −35° C. to −40° C. The residue obtained in step 1 is dissolved in tetrahydrofuran (200 ml) and added to the alkali metal amide solution prepared above for 20 minutes at −40° C. to −45° C. The reaction mass is stirred for 1 hour at −40° C. to −45° C. The solution is warmed to −25° C. to −30° C., methyl iodide (29.7 ml) is added for 1 hour at −25° C. to −30° C. and stirred for 30 minutes at −25° C. to −30° C. Saturated ammonium chloride (55 ml) is added to the reaction mass for 10 minutes at −25° C. to −30° C., the solution is then allowed to raise the temperature to 25° C., water (250 ml) is added at 25° C. and stirred for 10 minutes. Then the layers are separated and the organic layer is washed with 100 ml of 2N hydrochloric acid. The organic layer is again washed with water (300 ml), dried on sodium sulfate and concentrated to 150 ml at reduced pressure not allowing the temperature to raise above 50° C. to give N-methoxyethyl-7-[1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-[[2,2-dimethyl-butanoyl]oxy]-1(S)-naphthyl]-3(R),5(R)-dihydroxyheptanamide.

Provenance & Evidence