(5R)-6,7-dichloro-3,5-dimethyl-1,2,4,5-tetrahydro-3-benzazepine

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

Procedure: Compound 11 was prepared from (S)-9-bromo-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine utilizing a similar procedure as described herein for the preparation of Compound 9. 1H NMR (400 MHz, CDCl3) δ 7.18 (d, J=8 Hz, 1H), 6.92 (d, J=8 Hz, 1H), 3.94-3.88 (m, 1H), 3.29 (ddd, J=15, 12, 2 Hz, 1H), 2.98-2.93 (m, 1H), 2.90 (ddd, J=15, 6, 1 Hz; 1H), 2.36-2.32 (m, 4H) 2.13 (t, J=11 Hz, 1H), 1.33 (d, J=7 Hz, 3H). MS calculated for C12H15Cl2N+H: 288, observed: 288.

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

Procedure: Compound 11 was prepared from (S)-9-bromo-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine utilizing a similar procedure as described herein for the preparation of Compound 9. 1H NMR (400 MHz, CDCl3) δ 7.18 (d, J=8 Hz, 1H), 6.92 (d, J=8 Hz, 1H), 3.94-3.88 (m, 1H), 3.29 (ddd, J=15, 12, 2 Hz, 1H), 2.98-2.93 (m, 1H), 2.90 (ddd, J=15, 6, 1 Hz; 1H), 2.36-2.32 (m, 4H) 2.13 (t, J=11 Hz, 1H), 1.33 (d, J=7 Hz, 3H). MS calculated for C12H15Cl2N+H: 288, observed: 288.

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

Procedure: Compound 10 was prepared from (S)-8,9-dichloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine utilizing a similar procedure as described herein for the preparation of Compound 9. 1H NMR (400 MHz, CDCl3) δ 7.19 (d, J=8 Hz, 1H), 6.89 (d, J=8 Hz, 1H), 3.91-3.88 (m, 1H), 3.28 (ddd, J=15, 12, 2 Hz, 1H), 2.99-2.88 (m, 2H), 2.68 (ddd, J=15, 5, 1 Hz, 1H), 2.36-2.32 (m, 4H), 2.13 (t, J=11 Hz, 1H), 1.27 (d, J=7 Hz, 3H). MS calculated for C12H15Cl2N+H: 243, observed: 243.

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of (R)-8,9-dichloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.05 g, 0.20 mmol) in dichloroethane (3 mL) was treated with sodium triacetoxyborohydride (0.073 g, 0.35 mmol) and formaldehyde (0.017 mL, 37% solution in water). This was stirred at 20° C. for 2 h. The reaction was diluted with 15% NaOH and extracted with ethyl acetate (2×10 mL). The organics were dried with MgSO4, filtered and concentrated to give 0.042 g as an oil. 1H NMR (400 MHz, CDCl3) δ 7.19 (d, J=8 Hz, 1H), 6.89 (d, J=8 Hz, 1H), 3.91-3.88 (m, 1H), 3.28 (ddd, J=15, 12, 2 Hz, 1H), 2.99-2.88 (m, 2H), 2.68 (ddd, J=15, 5, 1 Hz, 1H), 2.36-2.32 (m, 4H), 2.13 (t, J=11 Hz, 1H), 1.27 (d, J=7 Hz, 3H). MS calculated for C12H15Cl2N+H: 243, observed: 243. extracted with ethyl acetate (2×10 mL) The organics were dried with MgSO4 filtered concentrated to give 0.042 g as an oil

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of (R)-8,9-dichloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.05 g, 0.20 mmol) in dichloroethane (3 mL) was treated with sodium triacetoxyborohydride (0.073 g, 0.35 mmol) and formaldehyde (0.017 mL, 37% solution in water). This was stirred at 20° C. for 2 h. The reaction was diluted with 15% NaOH and extracted with ethyl acetate (2×10 mL). The organics were dried with MgSO4, filtered and concentrated to give 0.042 g as an oil. 1H NMR (400 MHz, CDCl3) δ 7.19 (d, J=8 Hz, 1H), 6.89 (d, J=8 Hz, 1H), 3.91-3.88 (m, 1H), 3.28 (ddd, J=15, 12, 2 Hz, 1H), 2.99-2.88 (m, 2H), 2.68 (ddd, J=15, 5, 1 Hz, 1H), 2.36-2.32 (m, 4H), 2.13 (t, J=11 Hz, 1H), 1.27 (d, J=7 Hz, 3H). MS calculated for C12H15Cl2N+H: 243, observed: 243. extracted with ethyl acetate (2×10 mL) The organics were dried with MgSO4 filtered concentrated to give 0.042 g as an oil

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

Procedure: Compound 11 was prepared from (S)-9-bromo-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine utilizing a similar procedure as described herein for the preparation of Compound 9. 1H NMR (400 MHz, CDCl3) δ 7.18 (d, J=8 Hz, 1H), 6.92 (d, J=8 Hz, 1H), 3.94-3.88 (m, 1H), 3.29 (ddd, J=15, 12, 2 Hz, 1H), 2.98-2.93 (m, 1H), 2.90 (ddd, J=15, 6, 1 Hz, 1H), 2.36-2.32 (m, 4H)2.13 (t, J=11 Hz, 1H), 1.33 (d, J=7 Hz, 3H). MS calculated for C12H15Cl2N+H: 288, observed: 288.

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

Procedure: Compound 10 was prepared from (S)-8,9-dichloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine utilizing a similar procedure as described herein for the preparation of Compound 9. 1H NMR (400 MHz, CDCl3) δ 7.19 (d, J=8 Hz, 1H), 6.89 (d, I=8 Hz, 1H), 3.91-3.88 (m, 1H), 3.28 (ddd, J=15, 12, 2 Hz, 1H), 2.99-2.88 (m, 2H), 2.68 (ddd, J=15, 5, 1 Hz, 1H), 2.36-2.32 (m, 4H), 2.13 (t, J=11 Hz, 1H), 1.27 (d, J=7 Hz, 3H). MS calculated for C12H15Cl2N+H: 243, observed: 243.

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of (R)-8,9-dichloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.05 g, 0.20 mmol) in dichloroethane (3 mL) was treated with sodium triacetoxyborohydride (0.073 g, 0.35 mmol) and formaldehyde (0.017 mL, 37% solution in water). This was stirred at 20° C. for 2 h. The reaction was diluted with 15% NaOH and extracted with ethyl acetate (2×10 mL). The organics were dried with MgSO4, filtered and concentrated to give 0.042 g as an oil. 1H NMR (400 MHz, CDCl3) δ 7.19 (d, J=8 Hz, 1H), 6.89 (d, J=8 Hz, 1H), 3.91-3.88 (m, 1H), 3.28 (ddd, J=15, 12, 2 Hz, 1H), 2.99-2.88 (m, 2H), 2.68 (ddd, J=15, 5, 1 Hz, 1H), 2.36-2.32 (m, 4H), 2.13 (t, J=11 Hz, 1H), 1.27 (d, J=7 Hz, 3H). MS calculated for C12H15Cl2N+H: 243, observed: 243. extracted with ethyl acetate (2×10 mL) The organics were dried with MgSO4 filtered concentrated to give 0.042 g as an oil

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

Procedure: Compound 11 was prepared from (S)-9-bromo-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine utilizing a similar procedure as described herein for the preparation of Compound 9. 1H NMR (400 MHz, CDCl3) δ 7.18 (d, J=8 Hz, 1H), 6.92 (d, J=8 Hz, 1H), 3.94-3.88 (m, 1H), 3.29 (ddd, J=15, 12, 2 Hz, 1H), 2.98-2.93 (m, 1H), 2.90 (ddd, J=15, 6, 1 Hz; 1H), 2.36-2.32 (m, 4H) 2.13 (t, J=11 Hz, 1H), 1.33 (d, J=7 Hz, 3H). MS calculated for C12H15Cl2N+H: 288, observed: 288.

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

Procedure: Compound 10 was prepared from (S)-8,9-dichloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine utilizing a similar procedure as described herein for the preparation of Compound 9. 1H NMR (400 MHz, CDCl3) δ 7.19 (d, J=8 Hz, 1H), 6.89 (d, J=8 Hz, 1H), 3.91-3.88 (m, 1H), 3.28 (ddd, J=15, 12, 2 Hz, 1H), 2.99-2.88 (m, 2H), 2.68 (ddd, J=15, 5, 1 Hz, 1H), 2.36-2.32 (m, 4H), 2.13 (t, J=11 Hz, 1H), 1.27 (d, J=7 Hz, 3H). MS calculated for C12H15Cl2N+H: 243, observed: 243.

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of (R)-8,9-dichloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.05 g, 0.20 mmol) in dichloroethane (3 mL) was treated with sodium triacetoxyborohydride (0.073 g, 0.35 mmol) and formaldehyde (0.017 mL, 37% solution in water). This was stirred at 20° C. for 2 h. The reaction was diluted with 15% NaOH and extracted with ethyl acetate (2×10 mL). The organics were dried with MgSO4, filtered and concentrated to give 0.042 g as an oil. 1H NMR (400 MHz, CDCl3) δ 7.19 (d, J=8 Hz, 1H), 6.89 (d, J=8 Hz, 1H), 3.91-3.88 (m, 1H), 3.28 (ddd, J=15, 12, 2 Hz, 1H), 2.99-2.88 (m, 2H), 2.68 (ddd, J=15, 5, 1 Hz, 1H), 2.36-2.32 (m, 4H), 2.13 (t, J=11 Hz, 1H), 1.27 (d, J=7 Hz, 3H). MS calculated for C12H15Cl2N+H: 243, observed: 243. extracted with ethyl acetate (2×10 mL) The organics were dried with MgSO4 filtered concentrated to give 0.042 g as an oil