Ethyl Acetate → HCID 68162283, compound

Participants

Reaction Steps

1-methylethyl[(cis)-1-acetyl-6-(4-formylphenyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 7) (95 mg, 0.241 mmol) was dissolved in Dichloromethane (DCM) (2 mL) and to this was added tert-butyl 1 piperazinecarboxylate (67.3 mg, 0.361 mmol) as a solid and the resulting solution stirred under nitrogen for 40 min. sodium triacetoxyborohydride (66.4 mg, 0.313 mmol) was added and stirred as a suspension over the weekend. The reaction was quenched with ammonium chloride (2 ml). The organics were separated and the aqueous reextracted with DCM (5 ml). The combined organics were washed with water (5 ml) and reduced in vacuo to give a colourless solid. (135 mg). The solid was dissolved in DCM and loaded onto a 12+M silica cartridge for automated flash chromatography. A gradient of 20 to 100% ethyl acetate in iso-hexane over 10 CV was used and the appropriate fractions reduced in vacuo to give a colourless oil which was dried on high vac overnight (98 mg).

Provenance & Evidence