Triethylamine → HCID 59735082, compound

Participants

Reaction Steps

Methyl (1S,3R)-3-amino-1-isopropylcyclopentanecarboxylate hydrochloride (prepared in the same way as the intermediate from Step F, Procedure A, INTERMEDIATE 2, except with the modification that the methyl ester was employed instead of the benzyl ester, 1.4 g, 6.1 mmol) was combined with tetrahydro-4H-pyran-4-one (730 mg, 7.3 mmol), and triethylamine (1 mL, 7 mmol) in 50 mL of DCM. After 10 min, 4 Å powdered molecular sieves (1 g), and sodium triacetoxyborohydride (5.1 g, 24 mmol) were added and the resulting mixture was permitted to stir overnight. The reaction mixture was filtered through celite, and the filtrate was washed with saturated NaHCO3 solution twice, then once with brine. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated to afford 1 g of methyl (1S,3R)-1-isopropyl-3-(tetrahydro-2H-pyran-4-ylamino)cyclopentanecarboxylate.

Provenance & Evidence