4-bromo-N-[(2R)-1-hydroxypropan-2-yl]benzenesulfonamide

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

Procedure: (Trimethylsilyl)diazomethane (10 mL, 10 mmol) was added to a vigorously stirred mixture of 4-bromo-N-[(1R)-2-hydroxy-1-methylethyl]benzenesulfonamide (1.0 g, 3.4 mmol) and aqueous fluoroboric acid (conc. 42%, 6.8 mmol) in methylene chloride (25 mL), in 5 portions over 1 h at 0° C. The stirring was continued at 0° C. and another portion of trimethylsilyldiazomethane (5 mL, 5 mmol) was added over 30 min. The stirring was continued for 30 min, poured into water and extracted with methylene chloride. The organic phase was washed with water, dried over sodium sulfate and concentrated. Purification by column chromatography using gradient heptane to heptane/ethylacetate, (2:1), as the eluent gave 0.155 g (15% yield) of the title compound: MS (ESI) 309 m/z (M++1). was continued at 0° C. extracted with methylene chloride The organic phase was washed with water dried over sodium sulfate concentrated Purification by column chromatography

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

Procedure: (Trimethylsilyl)diazomethane (10 mL, 10 mmol) was added to a vigorously stirred mixture of 4-bromo-N-[(1R)-2-hydroxy-1-methylethyl]benzenesulfonamide (1.0 g, 3.4 mmol) and aqueous fluoroboric acid (conc. 42%, 6.8 mmol) in methylene chloride (25 mL), in 5 portions over 1 h at 0° C. The stirring was continued at 0° C. and another portion of trimethylsilyldiazomethane (5 mL, 5 mmol) was added over 30 min. The stirring was continued for 30 min, poured into water and extracted with methylene chloride. The organic phase was washed with water, dried over sodium sulfate and concentrated. Purification by column chromatography using gradient heptane to heptane/ethylacetate, (2:1), as the eluent gave 0.155 g (15% yield) of the title compound: MS (ESI) 309 m/z (M++1). was continued at 0° C. extracted with methylene chloride The organic phase was washed with water dried over sodium sulfate concentrated Purification by column chromatography

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

Procedure: (2R)-2-Aminopropan-1-ol (2.0 g, 26.7 mmol) and N-ethyl-N,N-diisopropylamine (8.5 mL, 48.9 mmol) was added dropwise over 20 min to a cooled (0° C.) solution of 4-bromobenzenesulfonyl chloride (6.12 g, 24 mmol) in methylene chloride (20 mL). The reaction mixture was allowed to stir for 1 h. Water was added and the mixture was washed, twice, with HCl (aq, 1 M) and one time with saturated aqueous sodium hydrogen carbonate. The organic phase was dried over sodium sulfate and evaporated to give 6.8 g, (96% yield) of the title compound: 1H NMR (CD3OD, 400 MHz) δ 7.82 (d, J=8 Hz, 2H), 7.76 (d, J=8 Hz, 2H), 3.44 (m, 1H), 3.34 (m, 3H), 1.03 (d, J=7 Hz, 3H); MS (ESI) m/z (M++1); 13C NMR (CD3OD, 100 MHz) 142.42, 133.36, 129.74, 127.90, 66.81, 52.49, 17.94 the mixture was washed The organic phase was dried over sodium sulfate evaporated

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

Procedure: (Trimethylsilyl)diazomethane (10 mL, 10 mmol) was added to a vigorously stirred mixture of 4-bromo-N-[(1R)-2-hydroxy-1-methylethyl]benzenesulfonamide (1.0 g, 3.4 mmol) and aqueous fluoroboric acid (conc. 42%, 6.8 mmol) in methylene chloride (25 mL), in 5 portions over 1 h at 0° C. The stirring was continued at 0° C. and another portion of trimethylsilyldiazomethane (5 mL, 5 mmol) was added over 30 min. The stirring was continued for 30 min, poured into water and extracted with methylene chloride. The organic phase was washed with water, dried over sodium sulfate and concentrated. Purification by column chromatography using gradient heptane to heptane/ethylacetate, (2:1), as the eluent gave 0.155 g (15% yield) of the title compound: MS (ESI) 309 m/z (M++1). was continued at 0° C. extracted with methylene chloride The organic phase was washed with water dried over sodium sulfate concentrated Purification by column chromatography

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

Procedure: (2R)-2-Aminopropan-1-ol (2.0 g, 26.7 mmol) and N-ethyl-N,N-diisopropylamine (8.5 mL, 48.9 mmol) was added dropwise over 20 min to a cooled (0° C.) solution of 4-bromobenzenesulfonyl chloride (6.12 g, 24 mmol) in methylene chloride (20 mL). The reaction mixture was allowed to stir for 1 h. Water was added and the mixture was washed, twice, with HCl (aq, 1 M) and one time with saturated aqueous sodium hydrogen carbonate. The organic phase was dried over sodium sulfate and evaporated to give 6.8 g, (96% yield) of the title compound: 1H NMR (CD3OD, 400 MHz) δ 7.82 (d, J=8 Hz, 2H), 7.76 (d, J=8 Hz, 2H), 3.44 (m, 1H), 3.34 (m, 3H), 1.03 (d, J=7 Hz, 3H); MS (ESI) m/z (M++1); 13C NMR (CD3OD, 100 MHz) 142.42, 133.36, 129.74, 127.90, 66.81, 52.49, 17.94 the mixture was washed The organic phase was dried over sodium sulfate evaporated