tert-butyl N-[(2R)-4-chloro-3-oxobutan-2-yl]carbamate

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

Procedure: Sodium borohydride (621 mg, 16.42 mmol) was added to a mixture of (R)-tert-butyl (4-chloro-3-oxobutan-2-yl)carbamate (910 mg, 4.10 mmol) in methanol (9 mL) at 0° C., and the mixture was stirred for one hour at 0° C. A few drops of acetic acid were added then the mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford tert-butyl ((2R)-4-chloro-3-hydroxybutan-2-yl)carbamate. 1H NMR (500 MHz, DMSO-d6) δ 6.65 (d, J=8.1 Hz, 1H), 5.24 (d, J=5.6 Hz, 1H), 3.58-3.53 (m, 1H), 3.50-3.44 (m, 2H), 3.44-3.34 (m, 1H), 1.36 (s, 9H), 0.99 (d, J=6.3, 3H). the mixture was concentrated under reduced pressure The residue was diluted with ethyl acetate washed with water dried over anhydrous magnesium sulfate filtered concentrated under reduced pressure

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

Procedure: Hydrochloric acid (2.0 M in water, 21.4 mL, 42.8 mmol) was added to a mixture of (R)-tert-butyl (4-diazo-3-oxobutan-2-yl)carbamate (1.89 g, 8.86 mmol) in diethyl ether (19.27 mL) at 0° C.0. The mixture was stirred vigorously for 20 minutes and then allowed to warm to room temperature and stirred vigorously until the mixture went from yellow to colorless. The mixture was washed with saturated aqueous sodium bicarbonate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford (R)-tert-butyl (4-chloro-3-oxobutan-2-yl)carbamate. 1H NMR (500 MHz, DMSO-d6) δ 7.34 (d, J=7.0 Hz, 1H), 4.64-4.51 (m, 2H), 4.23-4.02 (m, 1H), 1.36 (s, 9H), 1.16 (d, J=7.2 Hz, 3H). stirred vigorously until the mixture The mixture was washed with saturated aqueous sodium bicarbonate dried over anhydrous magnesium sulfate filtered concentrated under reduced pressure

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

Procedure: Hydrochloric acid (2.0 M in water, 21.4 mL, 42.8 mmol) was added to a mixture of (R)-tert-butyl (4-diazo-3-oxobutan-2-yl)carbamate (1.89 g, 8.86 mmol) in diethyl ether (19.27 mL) at 0° C.0. The mixture was stirred vigorously for 20 minutes and then allowed to warm to room temperature and stirred vigorously until the mixture went from yellow to colorless. The mixture was washed with saturated aqueous sodium bicarbonate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford (R)-tert-butyl (4-chloro-3-oxobutan-2-yl)carbamate. 1H NMR (500 MHz, DMSO-d6) δ 7.34 (d, J=7.0 Hz, 1H), 4.64-4.51 (m, 2H), 4.23-4.02 (m, 1H), 1.36 (s, 9H), 1.16 (d, J=7.2 Hz, 3H). stirred vigorously until the mixture The mixture was washed with saturated aqueous sodium bicarbonate dried over anhydrous magnesium sulfate filtered concentrated under reduced pressure

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

Procedure: Sodium borohydride (621 mg, 16.42 mmol) was added to a mixture of (R)-tert-butyl (4-chloro-3-oxobutan-2-yl)carbamate (910 mg, 4.10 mmol) in methanol (9 mL) at 0° C., and the mixture was stirred for one hour at 0° C. A few drops of acetic acid were added then the mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford tert-butyl ((2R)-4-chloro-3-hydroxybutan-2-yl)carbamate. 1H NMR (500 MHz, DMSO-d6) δ 6.65 (d, J=8.1 Hz, 1H), 5.24 (d, J=5.6 Hz, 1H), 3.58-3.53 (m, 1H), 3.50-3.44 (m, 2H), 3.44-3.34 (m, 1H), 1.36 (s, 9H), 0.99 (d, J=6.3, 3H). the mixture was concentrated under reduced pressure The residue was diluted with ethyl acetate washed with water dried over anhydrous magnesium sulfate filtered concentrated under reduced pressure

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

Procedure: Hydrochloric acid (2.0 M in water, 21.4 mL, 42.8 mmol) was added to a mixture of (R)-tert-butyl (4-diazo-3-oxobutan-2-yl)carbamate (1.89 g, 8.86 mmol) in diethyl ether (19.27 mL) at 0° C.0. The mixture was stirred vigorously for 20 minutes and then allowed to warm to room temperature and stirred vigorously until the mixture went from yellow to colorless. The mixture was washed with saturated aqueous sodium bicarbonate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford (R)-tert-butyl (4-chloro-3-oxobutan-2-yl)carbamate. 1H NMR (500 MHz, DMSO-d6) δ 7.34 (d, J=7.0 Hz, 1H), 4.64-4.51 (m, 2H), 4.23-4.02 (m, 1H), 1.36 (s, 9H), 1.16 (d, J=7.2 Hz, 3H). stirred vigorously until the mixture The mixture was washed with saturated aqueous sodium bicarbonate dried over anhydrous magnesium sulfate filtered concentrated under reduced pressure