Sodium triacetoxyborohydride → 2-{2-[(Adamantan-1-ylmethyl)-amino]4-bromo-phenyl}-malonic acid di-tert-butyl ester

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Reaction Steps

To a solution of adamantane-1-carbaldehyde (3.77 g, 23 mmol) in acetic acid (45 ml) was added 2-(2-amino-4-bromo-phenyl)-malonic acid di-tert-butyl ester (4.44 g, 11.5 mmol) followed by addition of sodium triacetoxyborohydride (3.41 g, 16 mmol). The reaction mixture stirred for 30 minutes. After removal of the acetic acid, the reaction mixture was then partitioned between water and chloroform. Powdered K2CO3 was added and the pH of the aqueous layer was adjusted to 8. After separation, the organic layer was then washed with brine, dried over MgSO4, filtered and concentrated under vacuum to give the crude title compound of 9A as a brown oil (7.81 9), which was used in the next step without further purification.

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