1-Methyl-3-pyrrolidinol → HCID 66803216, compound

HRID 341544Notes

Reaction equation

HRID 341544 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3]1.Cl[C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=1.O1CCC(OC2N=CC(C(OCC)=O)=CC=2)CC1>>[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([O:7][C:9]2[N:10]=[CH:11][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:18][CH:19]=2)[CH2:3]1

Participants

4

Reactant 3

HCID 930741-Methyl-3-pyrrolidinolHCID 2799611Ethyl 6-chloronicotinateHCID 66803133HCID 66803133, compound

Product 1

HCID 66803216HCID 66803216, compoundYield 25%

Procedure

Ethyl 6-[(1-methylpyrrolidin-3-yl)oxy]pyridine-3-carboxylate was prepared from 1-methylpyrrolidin-3-ol (0.161 g, 1.59 mmol) and ethyl 6-chloronicotinate (0.269 g, 1.45 mmol) according to the method described for Intermediate 236. The crude material was purified by FCC, eluting with a gradient of 0-20% MeOH in EtOAc to afford the title compound as a colourless oil (0.089 g, 25%). 1H NMR (250 MHZ, CDCl3) δ ppm 8.82 (1H, m), 8.13 (1H, dt), 6.74 (1H, m), 5.43 (1H, m), 4.39 (2H, dq), 2.82 (3H, m), 2.40 (3H, s), 2.39 (2H, m), 2.04 (1H, m) and 1.40 (3H, dt).

Workup

  1. customThe crude material was purified by FCC
  2. washeluting with a gradient of 0-20% MeOH in EtOAc

Sources & evidence

ORD record
ord-b259173e793644ebb4c1f0cd2f6412b7
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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