2,2-Dimethyl-1,3-dioxane-4,6-dione → 5-(4-(1H-1,2,4-triazol-1-yl)benzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 926565Notes

Reaction equation

N1CCC[C@H]1C(O)=O.[N:9]1([C:14]2[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=2)[CH:13]=[N:12][CH:11]=[N:10]1.N1(C2C=CC(CC(C(O)=O)C(O)=O)=CC=2)C=NC=N1.[CH3:41][C:42]1([CH3:50])[O:47][C:46](=[O:48])[CH2:45][C:44](=[O:49])[O:43]1.CC1NC(C)=C(C(OCC)=O)CC=1C(OCC)=O>C(O)C.C(O)(C)C>[N:9]1([C:14]2[CH:21]=[CH:20][C:17]([CH2:18][CH:45]3[C:46](=[O:48])[O:47][C:42]([CH3:50])([CH3:41])[O:43][C:44]3=[O:49])=[CH:16][CH:15]=2)[CH:13]=[N:12][CH:11]=[N:10]1

Participants

Conditions

Temperature: 23 °C

Procedure

L-Proline (1.81 g, 15.6 mmol) was added to a stirring, heterogeneous mixture of 4-(1H-1,2,4-triazol-1-yl)benzaldehyde (13.5 g, 78.0 mmol, Intermediate 82: step a) and 2,2-dimethyl-1,3-dioxane-4,6-dione (11.2 g, 78.0 mmol) in ethanol (520 mL) at 23° C. After 1.5 hours, diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate (19.7 g, 78.0 mmol) was added in one portion. After 16 hours, the ethanol was removed by rotary evaporation at 35° C. to afford a yellow solid. Isopropanol (300 mL) was added and the heterogeneous mixture was stirred for 10 minutes at 23° C. The mixture was filtered and the filter cake was washed with isopropanol (150 mL). The solids were collected and dried under vacuum to provide the titled compound as a white solid.

Workup

customat 23° C
waitAfter 16 hours
customthe ethanol was removed by rotary evaporation at 35° C.
customto afford a yellow solid
filtrationThe mixture was filtered
washthe filter cake was washed with isopropanol (150 mL)
customThe solids were collected
customdried under vacuum

Sources & evidence

ORD record: ord-c41f05ce4cf746899a384443f25e3e3a
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284308B2

Reaction notes

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