2-Tert-butyl 1'-(2-adamantyl) 1H-spiro[isoquinoline-4,4'-piperidine]-1',2(3H)-dicarboxylate → 2-adamantyl 2,3-dihydro-1H-spiro[isoquinoline-4,4'-piperidine]-1'-carboxylate

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Reaction Steps

2-Tert-butyl 1′-(2-adamantyl) 1H-spiro[isoquinoline-4,4′-piperidine]-1′,2(3H)-dicarboxylate (35 mg, 0.073 mmol) was dissolved in 1:2 TFA/CH2Cl2 (6 mL) and stirred for 30 min at rt. The mixture was concentrated to afford crude 2-adamantyl 2,3-dihydro-1H-spiro[isoquinoline-4,4′-piperidine]-1′-carboxylate (29 mg, quant). LC-MS Method 1 tR=1.48 min, m/z=381; 1H NMR (CD3OD) δ=7.52 (d, 1H), 7.38 (t, 1H), 7.28 (t, 1H), 7.21 (d, 1H), 4.85 (s, 1H), 4.38 (s, 2H), 4.19 (m, 2H), 3.68 (s, 2H), 3.28-3.01 (m, 2H).

Provenance & Evidence