Sodium hydride → tert-Butyl 4-(2-[(cyclopropylmethyl)(methylsulfonyl)amino]phenyl}piperidine-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a 100 mL round-bottomed flask was added tert-butyl 4-{2-[(methylsulfonyl)amino]phenyl}piperidine-carboxylate (Example 1 Step d) (1.9 grams, 5.4 mmol) and DMF (Aldrich) (30 mL). The solution was magnetically stirred vigorously at 25° C. under N2 atmosphere and treated in portions with NaH as a 60% dispersion in mineral oil (Aldrich) (150 mg, 6.4 mmol). After gas evolution ceased, (bromomethyl)cyclopropane (Aldrich) (675 μL, 940 mg, 7.0 mmol) was introduced via syringe. The reaction mixture was stirred at 25° C. for 15 h. The reaction was quenched by careful addition of satd NH4Cl (150 mL) and extracted with EtOAc (400 mL). The organic layer was washed with H2O (150 mL), satd NaCl (100 mL), dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound as a yellow foam (2.2 g). MS (ESI, pos. ion) m/z: 409 (M+1); (ESI, neg. ion) m/z: 407 (M−1). Calc'd for C21H32N2O4S: 408.56.

Provenance & Evidence