Hydrochloric Acid → HCID 18934737, compound

HRID 3332Notes

Reaction equation

Br[C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=[CH:6][CH:5]=[N:4][CH2:3]1.[Li]C(C)(C)C.Cl([O-])(=O)(=O)=O.[CH2:24]1[C:31]2[CH2:30][CH2:29][CH2:28][N+:27]=2[CH2:26][CH2:25]1.Cl>CCOCC.CCCCC>[C:8]1([C:2]2[CH:7]=[C:6]([C:31]34[CH2:30][CH2:29][CH2:28][N:27]3[CH2:26][CH2:25][CH2:24]4)[CH:5]=[N:4][CH:3]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: -30 °C

Procedure

3-Bromo-3-phenylpyridine (200 mg, 0.85 mmol) was dissolved in Et2O and cooled to -30° C. A solution of 2.5M t-BuLi (1.1 mL, 1.90 mmol) in pentane was added, and the reaction was stirred for 10 minutes. 1,2,3,5,6,7-Hexahydropyrrolizinium perchlorate (230 mg, 1.30 mmol) was added, and the reaction mixture was allowed to stir for 30 minutes at -30° C. then allowed to warm to room temperature and stir for 1 hour. Then 2N HCl was added, the phases were separated, and the aqueous phase was basified with 15% NaOH and extracted with CH2Cl2 (2×). The organic phases were combined, dried (MgSO4) and concentrated, and the residue was chromatographed (silica gel; CHCl3 /MeOH, 95:5) to afford a clear oil (32.5 mg).

Workup

stirringto stir for 30 minutes at -30° C.
temperatureto warm to room temperature
stirringstir for 1 hour
customthe phases were separated
extractionextracted with CH2Cl2 (2×)
dry with materialdried (MgSO4)
concentrationconcentrated
customthe residue was chromatographed (silica gel; CHCl3 /MeOH, 95:5)

Sources & evidence

ORD record: ord-5b22770333014a4da72ab520662759f7
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05733912

Reaction notes

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