Methyl Acrylate → (E)-3-{1'-Phenyl-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid methyl ester

HRID 518174Notes

Reaction equation

HRID 518174 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][C:10]3([CH2:21][C:20](=[O:22])[C:19]4[C:14](=[CH:15][CH:16]=[C:17](Br)[CH:18]=4)[O:13]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:24]([O:28][CH3:29])(=[O:27])[CH:25]=[CH2:26].COC(=O)/C=C/C1C=C2C(=CC=1)OC1(CCN(C(OC(C)(C)C)=O)CC1)CC2=O>>[CH3:29][O:28][C:24](=[O:27])/[CH:25]=[CH:26]/[C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[O:13][C:10]1([CH2:11][CH2:12][N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:8][CH2:9]1)[CH2:21][C:20]2=[O:22]

Participants

4

Reactant 3

HCID 7294Methyl AcrylateHCID 52952087(E)-3-{1'-tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid methyl esterHCID 669322201'-Phenyl-6-bromo-spiro[chromane-2,4'-piperidine]-4-one

Product 1

HCID 66932530(E)-3-{1'-Phenyl-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid methyl ester

Procedure

(E)-3-{1′-Phenyl-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester was synthesized starting from 1′-phenyl-6-bromo-spiro[chromane-2,4′-piperidine]-4-one (650 mg, 1.75 mmol) and methyl acrylate (541 mg, 6.2 mmol) according to the procedure described for Intermediate 1, Step B, giving 541 mg of the product.

Sources & evidence

ORD record
ord-d9db2f394610439f95759c5cb041fcb5
Source dataset
uspto-grants-2015_08
Patent number
US09115148B2

Reaction notes

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