Hydrochloric Acid → (E)-3-{4-oxo-spiro[chromane-2,4'-piperidine]-7-yl}-acrylic acid methyl ester

HRID 2046696Notes

Reaction equation

HRID 2046696 reaction equation
[CH3:1][O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:27]=[C:26]2[C:9]([C:10](=[O:28])[CH2:11][C:12]3([O:25]2)[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)=[CH:8][CH:7]=1.Cl.COC(=O)/C=C/C1C=C2C(=CC=1)OC1(CCNCC1)CC2=O>>[CH3:1][O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:27]=[C:26]2[C:9]([C:10](=[O:28])[CH2:11][C:12]3([O:25]2)[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]3)=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 52952088(E)-3-{1'-tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4'-piperidine]-7-yl}-acrylic acid methyl esterHCID 52952093(E)-3-{4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid methyl ester

Product 1

HCID 52952094(E)-3-{4-oxo-spiro[chromane-2,4'-piperidine]-7-yl}-acrylic acid methyl esterYield 107.7%

Procedure

(E)-3-{1′-tert-Butoxycarbonyl-4-oxo-spiro[chromane-2,4′-piperidine]-7-yl}-acrylic acid methyl ester (2.45 g, 6.1 mmol) was deprotected with HCl according to the procedure for preparation of Intermediate 1, Step C, giving (E)-3-{4-oxo-spiro[chromane-2,4′-piperidine]-7-yl}-acrylic acid methyl ester (1.98 g) as a yellow solid (hydrochloride salt).

Sources & evidence

ORD record
ord-5d487e1121bf46b087a4a18742ba4571
Source dataset
uspto-grants-2013_11
Patent number
US08592444B2

Reaction notes

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