Hydrochloric Acid → HCID 178515504, compound

HRID 2235278Notes

Reaction equation

C([Si](C)(C)[O:6][C@@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH2:9][CH2:8]1)(C)(C)C.[Li+].CC([N-]C(C)C)C.[Br:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36]Br)=[C:32]([Cl:38])[CH:31]=1.Cl>CO.O.C1COCC1>[Br:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH:15]2[CH2:16][CH2:17][N:13]([C@H:10]3[CH2:9][CH2:8][C@@H:7]([OH:6])[CH2:12][CH2:11]3)[C:14]2=[O:18])=[C:32]([Cl:38])[CH:31]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Charge a flask with cis-1-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-pyrrolidin-2-one (Preparation 17) (1.0 g, 3.4 mmol), dissolve with THF (0.2 M) and cool to −78° C. Add LDA (1.1 to 1.5 eq) and stir at −78° C. for 5 minutes. Add 4-bromo-1-bromomethyl-2-chloro-benzene (1.4 g, 5.0 mmol) and warm to room temperature overnight. Dilute with methanol (0.2 M) and add concentrated HCl (10 eq.) and stir at room temperature. Pour into water after reaction complete by HPLC and extract with methylene chloride, dry over sodium sulfate, filter and concentrate in vacuo. Purify the residue over silica gel (20% hexane in ethyl acetate) to afford 911 mg (70%) of the title compound: Mass spectrum (apci) m/z=387.9 (M+H).

Workup

customafter reaction complete by HPLC
extractionextract with methylene chloride
dry with materialdry over sodium sulfate
filtrationfilter
concentrationconcentrate in vacuo
customPurify the residue over silica gel (20% hexane in ethyl acetate)

Sources & evidence

ORD record: ord-3ee8ccc895934d36a77fb0df5c67f78b
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713979B2

Reaction notes

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