[1-(phenylmethoxymethyl)cyclobutyl]methanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 12.0 g (59.0 mmol) of {1-[(benzyloxy)methyl]cyclobutyl}methanol in 180 mL of dichloromethane was added 9.93 ml (70.8 mmol) of triethylamine at 0° C. followed by the addition of 5.02 mL (64.9 mmol) of methanesulfonyl chloride. After stirring for 2 h, saturated sodium chloride solution was added. The organic phase was isolated, dried using magnesium sulfate, and concentrated under vacuum to afford the crude product, which was used directly in the next step. 1H NMR (300 MHz, CDCl3) δ 7.39-7.32 (m, 5H), 4.57 (s, 2H), 4.30 (s, 2H), 3.52 (s, 2H), 2.98 (s, 3H), 1.95 (m, 6H). The organic phase was isolated dried concentrated under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 8.0 g (69 mmol) of [1-(hydroxymethyl)cyclobutyl]methanol in 120 ml of a 1:1 mixture of tetrahydrofuran:N,N-dimethylformamide was added 3.30 g (69 mmol) of a 60% dispersion of sodium hydride in oil and the contents stirred for 30 min. 8.6 mL (72.4 mmol) of benzyl bromide was then added and the contents stirred for 2 h. The reaction was quenched with aqueous ammonium chloride followed by the addition of diethyl ether. The organic phase was isolated, dried using magnesium sulfate, and concentrated under vacuum to afford the crude product which was purified by silica gel chromatography using ethyl acetate:hexane (3:7) as the eluent to afford 12.0 g (86%) of {1-[(benzyloxy)methyl]cyclobutyl}methanol as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 7.33-7.25 (m, 5H), 4.49 (s, 2H), 3.66 (d, J=6 Hz, 2H), 3.52 (s, 2H), 2.53 (t, J=6 Hz, 1H), 1.91-1.73 (m, 6H). GC-MS m/z 207 (M+H). the contents stirred for 2 h The reaction was quenched with aqueous ammonium chloride followed by the addition of diethyl ether The organic phase was isolated dried concentrated under vacuum to afford the crude product which was purified by silica gel chromatography