3-oxa-7-azabicyclo[3.3.1]nonan-9-one;hydrochloride

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred mixture of 3-oxa-7-aza-bicyclo[3.3.1]nonan-9-one hydrochloride [CAS #1228600-54-1] (4.80 g, 27 mmol), EtOAc (105 ml) and saturated aqueous Na2CO3 (105 ml) was added benzyl chloroformate (4.60 ml, 32.4 ml) at 0° C. The reaction mixture was stirred for 1 h at 0° C. and then extracted with EtOAc (2×). The organic phases were washed with brine, dried over Na2SO4, filtered and evaporated to dryness. Purification of the residue by normal phase column chromatography, eluting with heptane-EtOAc 1:1, gave the title compound as a colorless oil (5.75 g, 20.68 mmol, 77%): 1H-NMR (400 MHz, DMSO-d6): δ 2.31-2.35 (d, 2H), 2.34 dd, 2H), 3.78 (d, 2H), 4.19 (t, 2H), 4.55 (q, 2H), 5.11 (m, 2H), 7.28-7.38 (m, 5H). extracted with EtOAc (2×) The organic phases were washed with brine dried over Na2SO4 filtered evaporated to dryness Purification of the residue by normal phase column chromatography eluting with heptane-EtOAc 1:1

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred mixture of 3-oxa-7-aza-bicyclo[3.3.1]nonan-9-one hydrochloride [CAS #1228600-54-1] (4.80 g, 27 mmol), EtOAc (105 ml) and saturated aqueous Na2CO3 (105 ml) was added benzyl chloroformate (4.60 ml, 32.4 ml) at 0° C. The reaction mixture was stirred for 1 h at 0° C. and then extracted with EtOAc (2×). The organic phases were washed with brine, dried over Na2SO4, filtered and evaporated to dryness. Purification of the residue by normal phase column chromatography, eluting with heptane-EtOAc 1:1, gave the title compound as a colorless oil (5.75 g, 20.68 mmol, 77%): 1H-NMR (400 MHz, DMSO-d6): δ 2.31-2.35 (d, 2H), 2.34 dd, 2H), 3.78 (d, 2H), 4.19 (t, 2H), 4.55 (q, 2H), 5.11 (m, 2H), 7.28-7.38 (m, 5H). extracted with EtOAc (2×) The organic phases were washed with brine dried over Na2SO4 filtered evaporated to dryness Purification of the residue by normal phase column chromatography eluting with heptane-EtOAc 1:1