Lithium borohydride → (2-{[(4-Cyano-2-hydroxymethyl-benzyl)-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-pyridin-3-yl)-carbamic acid tert-butyl ester

Participants

Reaction Steps

To a cold (0° C.) solution of 2-{[(3-tert-Butoxycarbonylamino-pyridin-2-ylmethyl)-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-5-cyano-benzoic acid methyl ester (0.388 g, 0.77 mmol) in MeOH (7 mL) was added LiBH4 (107 mg, 4.91 mmol) and the mixture was allowed to warm to room temperature overnight. The mixture was concentrated and the residue was partitioned between CH2Cl2 (50 mL) and 1.0 N NaOH (15 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×15 mL). The combined organic extracts were dried (Na2SO4) and concentrated and provided 0.36 g of (2-{[(4-Cyano-2-hydroxymethyl-benzyl)-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-pyridin-3-yl)-carbamic acid tert-butyl ester as a white solid, which was used without further purification.

Provenance & Evidence