Methylamine → (R)-tert-butyl 3-((S)-1-(3-chlorophenyl)-1-hydroxy-5-(methylamino)-5-oxopentyl)piperidine-1-carboxylate

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Reaction Steps

(R)-tert-butyl 3-((S)-2-(3-chlorophenyl)-6-oxotetrahydro-2H-pyran-2-yl)piperidine-1-carboxylate (60 mg, 0.153 mmol) was dissolved in a ca 30% solution of methylamine in methanol (3 mL). The mixture was stirred at it for 2 h then concentrated under reduced pressure to give (R)-tert-butyl 3-((S)-1-(3-chlorophenyl)-1-hydroxy-5-(methylamino)-5-oxopentyl)piperidine-1-carboxylate (60 mg, 93%), which was used directly without purification. 1H NMR (400 MHz, CDCl3): 1.12-1.45 (m, 3H), 1.46 (s, 9H), 1.58-1.81 (m, 6H), 2.05-2.17 (m, 2H), 2.50-2.58 (m, 2H), 2.69 (m, 3H), 4.06 (m, 1H), 4.12-4.28 (m, 2H), 7.22-7.32 (m, 3H), 7.43 (s, 1H). MS (E/Z): 425 (M+H+).

Provenance & Evidence