Formaldehyde → HCID 69284554, compound

Participants

Reaction Steps

A solution of (1R,2S,5R)-isopropyl 5-(isopropylamino)-2-(2-(3-trifluoromethyl-benzamido)acetamido)cyclohexanecarboxylate (210 mg, 0.45 mmol; Example 11l) in 10 ml of CH2Cl2 is treated with 37% aqueous formaldehyde (0.5 ml) and NaBH(OAc)3 (0.3 g, 1.4 mmol) powder and stirred at room temperature for 2 hours. The mixture was treated with 1 N NaOH and stirred at room temperature for 1 hr and extracted into CH2Cl2. The extract was washed with water, brine, dried over Na2SO4, filtered and the solvent evaporated to give 200 mg of the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ(TMS): 8.16 (s, 1 H), 8.06 (d, J=7.8 Hz, 1 H), 7.86 (bt, 1 H), 7.75 (d, J=7.8 Hz, 1 H), 7.55 (t, J=7.8 Hz, 1 H), 7.21 (bs, 1 H), 4.91 (m, 1 H), 4.51 (m, 1 H), 4.12 (d, J=5.2 Hz, 2 H), 3.01 (m, 1 H), 2.58 (m, 1 H), 2.57 (m, 2 H), 2.21 (s, 3 H), 2.02-1.40 (m, 7 H), 1.16 (m, 6 H), 1.02 (m, 6 H). MS found: (M+H)+=486.46.

Provenance & Evidence