Hydrochloric Acid → (E)-3-{3,4-dihydro-3-methyl-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-6-yl}-acrylic acid methyl ester hydrochloride

HRID 2046706Notes

Reaction equation

HRID 2046706 reaction equation
[CH3:1][O:2][C:3](=[O:30])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][C:9]2[O:26][C:13]3([CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)[N:12]([CH3:27])[C:11](=[O:28])[C:10]=2[CH:29]=1.[ClH:31]>O1CCOCC1.C(Cl)Cl>[ClH:31].[CH3:1][O:2][C:3](=[O:30])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][C:9]2[O:26][C:13]3([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[N:12]([CH3:27])[C:11](=[O:28])[C:10]=2[CH:29]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66932109(E)-3-{1'-tert-butoxycarbonyl-3,4-dihydro-3-methyl-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-6-yl}-acrylic acid methyl ester

Product 1

HCID 66932520(E)-3-{3,4-dihydro-3-methyl-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-6-yl}-acrylic acid methyl ester hydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of (E)-3-{1′-tert-butoxycarbonyl-3,4-dihydro-3-methyl-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4′-piperidin]-6-yl}-acrylic acid methyl ester (3.00 g, 7.21 mmol) and 4 M HCl in dioxane (5 ml) in DCM (150 ml) was stirred at RT for 4 h. The precipitate was filtered off to give (E)-3-{3,4-dihydro-3-methyl-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4′-piperidin]-6-yl}-acrylic acid methyl ester hydrochloride (2.46 g).

Workup

  1. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-0307f885b94a4730a4e1723add3706eb
Source dataset
uspto-grants-2013_11
Patent number
US08592444B2

Reaction notes

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