Methyl Acrylate → (E)-3-{1'-tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4'-piperidine]-7-yl}-acrylic acid methyl ester

HRID 518150Notes

Reaction equation

HRID 518150 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([CH2:22][C:21](=[O:23])[C:20]3[C:15](=[CH:16][C:17](Br)=[CH:18][CH:19]=3)[O:14]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:25]([O:29][CH3:30])(=[O:28])[CH:26]=[CH2:27].COC(=O)/C=C/C1C=C2C(=CC=1)OC1(CCNCC1)CC2=O>>[CH3:30][O:29][C:25](=[O:28])/[CH:26]=[CH:27]/[C:17]1[CH:16]=[C:15]2[C:20]([C:21](=[O:23])[CH2:22][C:11]3([O:14]2)[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]3)=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 7294Methyl AcrylateHCID 27281806tert-Butyl 7-bromo-4-oxo-3,4-dihydro-1'H-spiro[1-benzopyran-2,4'-piperidine]-1'-carboxylateHCID 52952093(E)-3-{4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid methyl ester

Product 1

HCID 52952088(E)-3-{1'-tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4'-piperidine]-7-yl}-acrylic acid methyl ester

Procedure

7-Bromo-4-oxo-spiro[chromane-2,4′-piperidine]-1′-carboxylic acid tert-butyl ester (9.1 g, 23 mmol) was treated with methyl acrylate according to the procedure for preparation of Intermediate 1, Step B, giving (E)-3-{1′-tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4′-piperidine]-7-yl}-acrylic acid methyl ester (7.07 g) as a yellow solid.

Sources & evidence

ORD record
ord-a0ec6ec48aa64e04bd264ff160026100
Source dataset
uspto-grants-2015_08
Patent number
US09115148B2

Reaction notes

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