Potassium Carbonate → HCID 66932198, compound

HRID 518206Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].Br[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1.[CH3:17][O:18][C:19](=[O:45])/[CH:20]=[CH:21]/[C:22]1[CH:23]=[C:24]2[C:41](=[CH:42][CH:43]=1)[O:40][C:27]1([CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]1)[CH2:26][C:25]2=[O:44]>CC(C)=O>[CH3:17][O:18][C:19](=[O:45])/[CH:20]=[CH:21]/[C:22]1[CH:23]=[C:24]2[C:41](=[CH:42][CH:43]=1)[O:40][C:27]1([CH2:28][CH2:29][N:30]([CH2:8][CH2:9][C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)[CH2:31][CH2:32]1)[CH2:26][C:25]2=[O:44]

Participants

Conditions

Temperature: 50 °C

Procedure

K2CO3 (414 mg, 3 mmol) and 1-(2-bromo-ethyl)-4-fluoro-benzene (0.21 ml, 1.5 mmol) were added to a suspension of (E)-3-{4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (254 mg, 0.752 mmol, Intermediate 1, hydrochloride salt) in acetone (10 ml). The mixture was stirred at 50° C. for 54 h, then the solvent was evaporated and the residue was partitioned between water and DCM. The organic phase was dried, then evaporated and the crude residue was purified by column chromatography (eluent: DCM/MeOH 99:1 to 98:2) to give (E)-3-{1′-[2-(4-fluoro-phenyl)-ethyl]-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (300 mg) as a light yellow solid.

Workup

customthe solvent was evaporated
customthe residue was partitioned between water and DCM
customThe organic phase was dried
customevaporated
customthe crude residue was purified by column chromatography (eluent: DCM/MeOH 99:1 to 98:2)

Sources & evidence

ORD record: ord-8d4560a087ee454a9930eecbc0818225
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115148B2

Reaction notes

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