Water → tert-Butyl 4-(benzyloxy)piperidine-1-carboxylate

HRID 609771Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>C1COCC1>[CH2:17]([O:14][CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of N-tert-butoxycarbonylpiperidin-4-ol (25 g, 0.124 mol) in 100 ml anhydrous THF was added to a suspension of sodium hydride (5.96 g, 0.15 mol, pentane washed) in 100 ml anhydrous THF at 0° C. The reaction was stirred at 0° C. for 1 hour, then treated with a solution of benzyl bromide (25.65 g, 0.15 mol) in 20 ml anhydrous THF. The reaction was allowed to stand for 20 h at room temperature, cooled to 0° C., and 50 ml water was added cautiously. The product was extracted using ethyl acetate, the combined organic extracts were washed with water, dried (MgSO4) and concentrated. Chromatography using petroleum ether→20% ethyl acetate-petroleum ether gave 4-benzyloxy-1-tert-butoxycarbonyl-piperidine as a colourless solid. δH (250 MHz, CDCl3) 1.45 (9H, s), 1.51-1.65 (2H, m), 1.80-1.94 (2H, m), 3.04-3.15 (2H, m), 3.51-3.61 (1H, m), 3.70-3.84 (2H, m), 4.56 (2H, m), 7.26-7.35 (5H, m). m/e (ES) 292.

Workup

waitto stand for 20 h at room temperature
temperaturecooled to 0° C.
extractionThe product was extracted
washthe combined organic extracts were washed with water
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-e921a7804eea47ffa65ec061b3dca03f
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05998440

Reaction notes

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