Aluminium lithium hydride → Tert-butyl 3-(hydroxymethyl)-3-methylpiperidine-1-carboxylate

Participants

Reaction Steps

To a 0° C. stirred solution of Intermediate 54 (1.17 g, 4.56 mmol) in dry THF (20 ml) was added LiAlH4 (1.0 M in THF, 9.11 ml, 9.11 mmol) dropwise and the reaction was allowed to warm to room temperature. Upon completion as indicated by TLC, the reaction was carefully quenched with saturated NH4Cl and EtOAc was added. The layers were separated, the aqueous layer was extracted with EtOAc (3×15 ml) and the organic extracts were combined. The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure to yield 0.844 g (42.1%) of 3-hydroxymethyl-3-methyl-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 55). 1H NMR (400 MHz, CDCl3) δ ppm 0.9 (s, 3 H), 1.3 (m, 2 H), 1.5 (s, 9 H), 1.5 (m, 3 H), 2.9 (s, 1 H), 3.1 (s, 1 H), 3.5 (d, J=11.5 Hz, 1 H), 3.8 (m, 2 H).

Provenance & Evidence