Tert-butyl 4-hydroxypiperidine-1-carboxylate → tert-Butyl 4-[(3-methylpyridin-4-yl)oxy]piperidine-1-carboxylate

HRID 222328Notes

Reaction equation

HRID 222328 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.Cl[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][C:18]=1[CH3:23]>>[CH3:23][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:17]=1[O:14][CH:11]1[CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][CH2:10]1

Participants

3

Reactant 2

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 162176554-Chloro-3-methylpyridine hydrochloride

Product 1

HCID 57753828tert-Butyl 4-[(3-methylpyridin-4-yl)oxy]piperidine-1-carboxylate

Procedure

The title compound was prepared from 1-Boc-4-hydroxypiperidine and 4-chloro-3-methylpyridine hydrochloride, using a similar method to preparation 27. The reaction mixture was stirred for 72 hours to afford the title compound the desired product in 87% yield. 1H NMR (CDCl3, 400 MHz) δ: 1.44 (s, 9H), 1.75-1.85 (m, 2H), 1.87-1.97 (m, 2H), 2.18 (s, 3H), 3.42-3.53 (m, 2H), 3.56-3.65 (m, 2H), 4.57-4.65 (m, 1H), 6.72 (d, 1H), 8.29 (s, 1H), 8.35 (d, 1H); LRMS APCI m/z 293 [M+H]+

Workup

  1. customto preparation 27

Sources & evidence

ORD record
ord-f5d904e1ec6f4803904e34bcf65e263f
Source dataset
uspto-grants-2012_06
Patent number
US08207198B2

Reaction notes

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