Dichloromethane → (7R,7aR)-2-Chloro-4-(7-hydroxy-7a-methyl-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl)-3-methylbenzonitrile

HRID 501613Notes

Reaction equation

[Si]([O:8][C@H:9]1[C@@:16]2([CH3:17])[N:12]([C:13](=[O:29])[N:14]([C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([Cl:27])[C:20]=3[CH3:28])[C:15]2=[O:18])[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.C([O-])(O)=O.[Na+].C(Cl)Cl>C1COCC1>[Cl:27][C:21]1[C:20]([CH3:28])=[C:19]([N:14]2[C:15](=[O:18])[C@@:16]3([CH3:17])[C@H:9]([OH:8])[CH2:10][CH2:11][N:12]3[C:13]2=[O:29])[CH:26]=[CH:25][C:22]=1[C:23]#[N:24]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (7R,7aR)-4-[7-(tert-Butyldimethylsilanyloxy)-7a-methyl-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl]-2-chloro-3-methylbenzonitrile (60B) (32 mg, 0.07 mmol) in THF (2 mL) in a plastic vial was cooled to 0° C. HF/pyridine complex (0.12 mL) was added and the reaction was stirred at 0° C. for 1 h and at rt overnight. Saturated aqueous NaHCO3 and CH2Cl2 were added. The layers were separated and the organic layer was concentrated under reduced pressure. The residue was purified via chromatography (silica gel) eluting with 75% EtOAc in hexane to provide the title compound (16 mg). LC/MS m/z 320 [M+H]+.

Workup

additionHF/pyridine complex (0.12 mL) was added
customThe layers were separated
concentrationthe organic layer was concentrated under reduced pressure
customThe residue was purified via chromatography (silica gel)
washeluting with 75% EtOAc in hexane

Sources & evidence

ORD record: ord-8c9da2874b74464abd5d9b667123e147
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772267B2

Reaction notes

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