p-Toluenesulfonic acid → HCID 86746067, compound

Participants

Reaction Conditions

Reaction Steps

A 5.00 g (21.43 mmol) sample of 4-piperidinone benzyl carbamate, from Step 2 Example 196, 4.69 mL (53.59 mmol) of 3-bromo-1,2-propanediol, and 0.200 g (1.07 mmol) of p-toluenesulfonic acid was added to 100 mL of toluene and the mixture was heated at 110° C. for 24 hours. The reaction solution was poured into 200 mL of 7% sodium bicarbonate solution, washed well, washed with water, dried over anhydrous sodium sulfate and the solvent removed under vacuum to afford 7.79 g of 2-bromomethyl-1,4-dioxa-8-azaspiro[4.5]decane benzyl carbamate, MS (DCl) M/Z 387 (M+NH4), 370 (M+H). NMR (CDCl3): d 1.69 (m, 4H), 3.31 (dd, 1H, J=9.0, 10.5 Hz), 3.44 (dd, 1H, J=6.0, 9.0 Hz), 3.58 (m, 4H), 3.90 (dd, 1H, J=6.0, 9.0 Hz), 4.14 (dd, 1H, J=6.0, 9.0 Hz), 4.37 (m, 1H), 5.13 (s, 2H), 7.34 (m, 5H).

Provenance & Evidence