tert-butyl N-[(4-methoxyphenyl)methyl]carbamate

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

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

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

Procedure: To a suspension of NaH (60%, 157 mg, 3.93 mmol) in THF (5 mL) at 0° C. was added tert-butyl (4-methoxybenzyl)carbamate (889 mg, 3.75 mmol) in THF (5 mL). After stirring for 30 minutes at 0° C., diisopropyl(vinyl)phosphine oxide (300 mg, 1.873 mmol) in THF (3 mL) was added. The reaction was allowed to slowly warn to room temperature and subsequently heated to 60° C. for 3 h. The mixture was quenched with saturated NH4Cl and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), and evaporated. Flash chromatography (0-10% MeOH/EtOAc) afforded the title compound as a pale yellow oil. MS: cal'd 398 (MH+), exp 398 (MH+). to slowly warn to room temperature subsequently heated to 60° C. for 3 h The mixture was quenched with saturated NH4Cl extracted with EtOAc (2×) The combined organic layers were washed with brine dried (MgSO4) evaporated

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

Procedure: To a suspension of NaH (60%, 157 mg, 3.93 mmol) in THF (5 mL) at 0° C. was added tert-butyl (4-methoxybenzyl)carbamate (889 mg, 3.75 mmol) in THF (5 mL). After stirring for 30 minutes at 0° C., diisopropyl(vinyl)phosphine oxide (300 mg, 1.873 mmol) in THF (3 mL) was added. The reaction was allowed to slowly warn to room temperature and subsequently heated to 60° C. for 3 h. The mixture was quenched with saturated NH4Cl and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), and evaporated. Flash chromatography (0-10% MeOH/EtOAc) afforded the title compound as a pale yellow oil. MS: cal'd 398 (MH+), exp 398 (MH+). to slowly warn to room temperature subsequently heated to 60° C. for 3 h The mixture was quenched with saturated NH4Cl extracted with EtOAc (2×) The combined organic layers were washed with brine dried (MgSO4) evaporated

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

Procedure: To a suspension of NaH (60%, 157 mg, 3.93 mmol) in THF (5 mL) at 0° C. was added tert-butyl (4-methoxybenzyl)carbamate (889 mg, 3.75 mmol) in THF (5 mL). After stirring for 30 minutes at 0° C., diisopropyl(vinyl)phosphine oxide (300 mg, 1.873 mmol) in THF (3 mL) was added. The reaction was allowed to slowly warn to room temperature and subsequently heated to 60° C. for 3 h. The mixture was quenched with saturated NH4Cl and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), and evaporated. Flash chromatography (0-10% MeOH/EtOAc) afforded the title compound as a pale yellow oil. MS: cal'd 398 (MH+), exp 398 (MH+). to slowly warn to room temperature subsequently heated to 60° C. for 3 h The mixture was quenched with saturated NH4Cl extracted with EtOAc (2×) The combined organic layers were washed with brine dried (MgSO4) evaporated