Hydrochloric Acid → 4-(2,4,6-trimethoxyphenyl)-6-(hydroxymethyl)pyridine-2-carboxylic Acid Ethyl Ester

HRID 655900Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([O:11][CH3:12])[C:4]=1[C:13]1[CH:18]=[C:17]([C:19](OCC)=[O:20])[N:16]=[C:15]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:14]=1.[BH4-].[Na+].Cl>C(O)C>[CH2:27]([O:26][C:24]([C:15]1[CH:14]=[C:13]([C:4]2[C:3]([O:2][CH3:1])=[CH:8][C:7]([O:9][CH3:10])=[CH:6][C:5]=2[O:11][CH3:12])[CH:18]=[C:17]([CH2:19][OH:20])[N:16]=1)=[O:25])[CH3:28]

Participants

Conditions

Temperature: 45 °C

Procedure

Compound 12 (2.83 g, 7.27 mmol) was suspended in ethanol (140 mL), and the mixture was heated to 45° C. Sodium borohydride (0.29 g) was added, and the mixture was stirred for 1 h and allowed to cool to room temperature. pH of the solution was adjusted to 3 with 6 M HCl and concentrated. The residue was suspended in dichloromethane and washed with sat. NaHCO3. The organic layer was dried over Na2SO4 and purified on silica gel (eluent petroleum ether bp 40-60° C.:ethyl acetate:triethylamine, 2:5:1; v/v/v). ESI-MS: [M+H]+ 348.14 calc. for C18H22NO6+ 348.14.

Workup

temperatureto cool to room temperature
concentrationconcentrated
washwashed with sat. NaHCO3
dry with materialThe organic layer was dried over Na2SO4
custompurified on silica gel (eluent petroleum ether bp 40-60° C.:ethyl acetate:triethylamine, 2:5:1; v/v/v)

Sources & evidence

ORD record: ord-d9f3f19afdd14e95a2ded9984cc47c2b
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071626B2

Reaction notes

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