Dimethylformamide dimethyl acetal → tert-Butyl 3-[(dimethylamino)methylidene]-4-oxopyrrolidine-1-carboxylate

HRID 1052036Notes

Reaction equation

HRID 1052036 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.CO[CH:16](OC)[N:17]([CH3:19])[CH3:18]>O1CCOCC1>[C:10]([O:9][C:7]([N:4]1[CH2:3][C:2](=[O:1])[C:6](=[CH:16][N:17]([CH3:19])[CH3:18])[CH2:5]1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylate

Product 1

HCID 53415260tert-Butyl 3-[(dimethylamino)methylidene]-4-oxopyrrolidine-1-carboxylateYield 46.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (25.0 g, 135 mmol), dimethylformamide dimethylacetal (27 mL, 202 mmol) and 1,4-dioxane (170 mL) was heated at 100° C. for 17 hours. The dioxane was removed in vacuo. The resulting red solid was triturated with hexanes (180 mL) for one hour, and filtered. The solid was rinsed with hexanes (2×80 mL) and air dried. Chromatography on silica gel eluting with dichloromethane:methanol 39:1 then 19:1 to give the title compound (15.04 g, 46%).

Workup

  1. customThe dioxane was removed in vacuo
  2. customThe resulting red solid was triturated with hexanes (180 mL) for one hour
  3. filtrationfiltered
  4. washThe solid was rinsed with hexanes (2×80 mL) and air
  5. customdried

Sources & evidence

ORD record
ord-ece6e66ebe2343ffb7de7683c57dd1a0
Source dataset
uspto-grants-2016_07
Patent number
US09388176B2

Reaction notes

Loading…