Lithium borohydride → 1-methylethyl {(cis)-1-acetyl-6-[4-(hydroxymethyl)-1H-imidazol-1-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 1-[(cis)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-imidazole-4-carboxylate (for a preparation see Example 90) (857 mg, 2 mmol) in dry THF (10 mL) was cooled to 0° C. and treated with 2M lithium borohydride in THF (2 mL, 4 mmol). The reaction mixture was stirred at room temperature for 8 h then was partitioned between AcOEt (10 mL) and a saturated NH4Cl aqueous solution (10 mL). The layers were separated. The aqueous phase was extracted with AcOEt (2×10 mL). The combined organic phases were dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 0 to 10% MeOH in DCM) gave 1-methylethyl {(cis)-1-acetyl-6-[4-(hydroxymethyl)-1H-imidazol-1-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate (440 mg, 1.139 mmol, 57%) as a colourless foam.

Provenance & Evidence