Sodium Acetate → tert-Butyl 4-(2-oxoethyl)piperidine-1-carboxylate

Participants

Reaction Steps

A solution of CH2Cl2 (200 mL) was treated with pyridiniumchlorochromate (PCC) (6.7 g, 0.031 mol) for five minutes. Solid NaOAc (2.55 g, 0.031 mol) and 4Å molecular sieves were added, followed by a solution of 4-1 (4.75 g, 0.02 mol) in CH2Cl2 (50 mL). The reaction was stirred for 3 h, diluted with 400 mL of Et2O, and filtered through a pad of silica gel. The silica gel was washed with 1 L of Et2O and 0.5 L of 1:1 Et2O/CHCl3. The organic solutions were combined, concentrated to give a greenish oil which was filtered through another pad of silica gel, eluting with 1.2 L of Et2O. The filtrate was concentrated to give 4-2 as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 9.77 (s, 1H), 4.08 (bd, 2H), 2.7 (bt, 2H), 2.37 (dd, 2H), 2.03 (m, 1H), 1.7 (bd, 2H), 1.42 (s, 9H), 1.2 (m, 2H). ##STR32## Methyl 2-(S)-benzyloxycarbonylamino-3-aminopropionate hydrochloride (5-2)

Provenance & Evidence