3-Hydroxypyridine → 2-(Pyridin-3-yl-oxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 2191239Notes

Reaction equation

HRID 2191239 reaction equation
[O:1]([CH2:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:2]1[CH:7]=C[CH:5]=[CH:4][CH:3]=1.OC1C=[N:24]C=CC=1>>[C:17]([O:16][C:14]([N:10]1[CH2:11][CH2:12][CH2:13][CH:9]1[CH2:8][O:1][C:2]1[CH:7]=[N:24][CH:5]=[CH:4][CH:3]=1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

3

Reactant 2

HCID 79713-HydroxypyridineHCID 10636271(S)-tert-Butyl 2-(phenoxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 218517822-(Pyridin-3-yl-oxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl esterYield 61%

Procedure

2-(Pyridin-3-yl-oxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (19) was prepared according to the same procedure for compound 9, except using 3-hydroxypyridine. The crude product was purified with ether to afford 1.70 g (61%) of 19 as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 8.32 (s, 1H), 8.21 (s, 1H), 7.21 (m, 2H), 4.16 (m, 2H), 3.99-3.86 (m, 1H), 3.38 (m, 2H), 2.05-1.84 (m, 4H), 1.47 (s, 9H).

Workup

  1. custom2-(Pyridin-3-yl-oxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (19) was prepared
  2. customThe crude product was purified with ether

Sources & evidence

ORD record
ord-0a8616bc41e044808ac594c86f1f04c2
Source dataset
uspto-grants-2012_12
Patent number
US08329686B2

Reaction notes

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