tert-Butyl (S)-2-(2,2-dimethyl-4,6-dioxo-1,3-dioxane-5-carbonyl)pyrrolidine-1-carboxylate → Tert-butyl (3-oxopropanoyl)-1-pyrrolidinecarboxylate

HRID 458394Notes

Reaction equation

CC1(C)OC(=O)[CH:5]([C:9]([C@@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:10])[C:4](=O)[O:3]1>C1(C)C=CC=CC=1>[O:3]=[CH:4][CH2:5][C:9]([CH:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:10]

Participants

Conditions

Temperature: 80 °C

Procedure

ArgoGel-OH (45 g, 0.49 meq/g, 22 mmol) was suspended in toluene (400 mL) and tert-butyl (2S)-2-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)carbonyl]-1-pyrrolidinecarboxylate (60. g, 176 mmol) was added. The sealed reaction tube was heated at 80° C. for 23 h. The reaction mixture was allowed to cool to room temperature and filtered. The resin was washed (DMF then DCM then ether; 8× each) then dried at 40° C. overnight under high vacuum (63 g; 0.44 meq/g).

Workup

customThe sealed reaction tube
temperatureto cool to room temperature
filtrationfiltered
washThe resin was washed (DMF
custom8× each) then dried at 40° C. overnight under high vacuum (63 g; 0.44 meq/g)

Sources & evidence

ORD record: ord-90a804577e34449da10d0f04fe6b99e1
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07189851B2

Reaction notes

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