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

HRID 751128Notes

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-6d60b932aee04e55beb4c909c3f4b740
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405234B2

Reaction notes

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