(S)-tert-Butyl 2-(phenoxymethyl)pyrrolidine-1-carboxylate → 2-(Pyridin-4-yl-oxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 2191243Notes

Reaction equation

HRID 2191243 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]=[CH:6]C=[CH:4][CH:3]=1.OC1C=C[N:25]=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]=[CH:6][N:25]=[CH:4][CH:3]=1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

3

Reactant 2

HCID 10636271(S)-tert-Butyl 2-(phenoxymethyl)pyrrolidine-1-carboxylateHCID 178418642HCID 178418642, compound

Product 1

HCID 689337972-(Pyridin-4-yl-oxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl esterYield 47%

Procedure

2-(Pyridin-4-yl-oxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (22) was prepared according to the same procedure for compound 9, except using 4-hydroxypyridine. The crude product was purified with ethyl acetate to afford 1.31 g (47%) of 22 as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 8.42 (m, 2H), 6.87 (m, 2H), 4.15 (m, 3H), 3.43 (m, 2H), 1.98 (m, 4H), 1.50 (s, 9H).

Workup

  1. custom2-(Pyridin-4-yl-oxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (22) was prepared
  2. customThe crude product was purified with ethyl acetate

Sources & evidence

ORD record
ord-0a65fe1cf0dd4e3ab5a9d42464fcc599
Source dataset
uspto-grants-2012_12
Patent number
US08329686B2

Reaction notes

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