Isocaproaldehyde → N-Butyl-gamma-hydroxy-alpha-methyl-delta-[(4-methylpentyl)amino]cyclohexanehexanamide hydrochloride

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Reaction Steps

To a solution of [αS-(αR*,γR*,δR*)]δ-amino-N-butyl-γ-hydroxy-α-methyl-cyclohexanehexanamide (II: 0.17 g, 0.57 mmol) and 4-methylvaleraldehyde (0.063 g, 0.63 mmol) in CH2Cl2 (3 mL) was added NaBH(OAc)3 (0.181 g, 0.86 mmol) and glacial acetic acid (0.05 mL). The mixture was stirred at r.t. for 16 h. The reaction was made basic (pH=8) by the addition of sat aqueous NaHCO3 and extracted with CH2Cl2. The organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. Silica gel chromatography (19:19:1 0.05 CHCl3 :Et2O:MeOH:NH4OH) of the concentrate gave the free amine (0.128 g, 59%) which was converted to its hydrochloride salt by the addition of 1.5N ethanolic HCl (0.3 mL). Removal of solvent in vacuo gave the title compound (0.128 g, 59%) as an amorphous white solid, mp 65° C.

Provenance & Evidence