Lithium Hydroxide → 2-(2-allyl-1-(tert-butoxycarbonyl)-1H-indol-3-yl)acetic acid

Participants

Reaction Steps

To a solution of tert-butyl 2-allyl-3-(2-methoxy-2-oxoethyl)-1H-indole-1-carboxylate (0.94 g, 2.74 mmol) in THF (15 mL) and MeOH (5 mL) was added a solution of LiOH (170 mg, 6.8 mmol) in H2O (5 mL). The solution was stirred for 2 h. The reaction was partitioned between EtOAc and 20% aqueous KH2PO4. The organics were separated, dried over sodium sulfate, and the solvents removed in vacuo to provide 2-(2-allyl-1-(tert-butoxycarbonyl)-1H-indol-3-yl)acetic acid (900 mg). MS (m/z) 316 [M+H]+.

Provenance & Evidence