Lithium diisopropylamide → HCID 89463048, compound

Participants

Reaction Conditions

Reaction Steps

An ice cold mixture of 2-(1-benzyl-6-methyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-(tert-butoxy)acetic acid (200 mg, 0.423 mmol) in Tetrahydrofuran (THF) (2.0 mL) was treated with dropwise addition of LDA, 2M solution in heptane/THF/ethylbenzene (0.423 mL, 0.846 mmol) and then allowed to stir at 0° C. for 20 minutes. Additional LDA (0.212 mL, 0.423 mmol) was added and then stirred an additional 20 minutes. The mixture was quenched by adding 1N HCl, acidified to pH 2 and then extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, filtered and concentrated to give the crude debenzylation product which was used crude in the next step. LC/MS (m/z) ES+=369 (M+1).

Provenance & Evidence