Ethyl Acetate → 1-(2-nitrobenzyl)pyrrolidine

HRID 2376154Notes

Reaction equation

Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N+:9]([O-:11])=[O:10].[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>CN(C=O)C.[Cl-].[Na+].O>[N+:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)([O-:11])=[O:10]

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of 1-(bromomethyl)-2-nitrobenzene (2.10 g) in DMF (20 mL) was added pyrrolidine (0.95 mL) and N,N-diisopropylethylamine (2.54 mL), and the mixture was stirred at 60° C. for 24 hours. The resulting mixture was poured into ethyl acetate and brine. The organic phase was separated and washed with brine, dried over sodium sulfate. The solvent was evaporated in vacuo and the residue was purified by silica gel column chromatography to give 1-(2-nitrobenzyl)pyrrolidine (1.92 g) as a pale yellow oil.

Workup

customThe organic phase was separated
washwashed with brine
dry with materialdried over sodium sulfate
customThe solvent was evaporated in vacuo
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-d5a0f1a6e5744dada8e6357f209451ac
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465731B2

Reaction notes

Loading…