Water → 3-((1S,3S)-3-azido-indan-1-yl)-1H-indole

Participants

Reaction Conditions

Reaction Steps

1,8-Diazabicyclo[5.4.0]undec-7-ene (4.8 mL, 32.1 mmol, 1.45 equiv) was added to (1R,3S)-3-(1H-indol-3-yl)-indan-1-ol (22.2 mmol ) and diphenyl phosphoryl azide (6.0 mL, 27.8 mmol, 1.25 equiv) in 150 mL dry THF at 0° C. The reaction was stirred 0.5 hours at 0° C., then 2 hours at room temperature—TLC showed full conversion. The reaction mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with 100 mL 0.5 N HCl, sat. NaHCO3, dried over MgSO4 and concentrated in vacuo to give the 3-((1S,3S)-3-azido-indan-1-yl)-1H-indole.

Provenance & Evidence