Tert-butyl 3-(2,6-dichloro-4-pyridyl)-2,5-dihydropyrrole-1-carboxylate → Tert-butyl 3-(2,6-dichloropyridin-4-yl)pyrrolidine-1-carboxylate

HRID 1057047Notes

Reaction equation

HRID 1057047 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH:12]=2)[CH:5]=[C:4]([Cl:20])[N:3]=1>[Rh]>[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:9]2)[CH:5]=[C:4]([Cl:20])[N:3]=1

Participants

3

Reactant 1

HCID 90016160Tert-butyl 3-(2,6-dichloro-4-pyridyl)-2,5-dihydropyrrole-1-carboxylate

Product 1

HCID 90015021Tert-butyl 3-(2,6-dichloropyridin-4-yl)pyrrolidine-1-carboxylateYield 95.6%

Reagents, catalysts & solvents 1

HCID 23948RhodiumCatalyst

Procedure

A mixture of tert-butyl 3-(2,6-dichloro-4-pyridyl)-2,5-dihydropyrrole-1-carboxylate (126 mg, 0.399 mmol) and 5% Rh/C (20 mg) in absolute alcohol (12 mL) was purged with N2, then primed with H2 (balloon)/vacuum (3×), stirred under H2 balloon for o/n. It was purged with N2, filtered through Celite, washed the Celite with MeOH, concentrated in vacuo gave 121 mg (95.4%) of product as clear gum. It was carried on without further purification. LC-MS: m/z=318 (M+H+).

Workup

  1. customwas purged with N2
  2. customIt was purged with N2
  3. filtrationfiltered through Celite
  4. washwashed the Celite with MeOH
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ed8503bd9db04ac2b049b91a9ec641a9
Source dataset
uspto-grants-2016_07
Patent number
US09399636B2

Reaction notes

Loading…