Sodium triacetoxyborohydride → HCID 21022369, compound

Participants

Reaction Steps

To a solution of 36 (136 mg, 0.433 mmol) in MeOH (5 ml) was added (1,1-dimethyl-3-oxo-propyl)-carbamic acid tert-butyl ester(105 mg, 0.522 mmol) followed by NaBH(OAc)3 (138 mg, 0.65 mmol). The reaction mixture was stirred at room temperature overnight, quenched with water. Solvent was removed in vacuo, the residue was purified by preparative HPLC to give 37 (86 mg) at the yield of 41% for the two steps. 1H-NMR (500 MHz, CDCl3): δ 7.23–7.39 (m, 5H), 5.89 (d, J=16.0 Hz, 1H), 5.01 (d, J=16.0 Hz, 1H), 4.66 (t, J=5.77 Hz, 1H), 4.43 (brs, 1H), 2.86 (s, 3H), 2.45 (m, 2H), 2.11 (m, 1H), 1.96 (m, 2H), 1.74 (m, 1H), 1.30 (s, 9H), 1.13 (s, 3H), 1.01 (s, 3H), 0.88 (t, J=7.42 Hz, 3H).

Provenance & Evidence