Water → HCID 68648645, compound

HRID 1502526Notes

Reaction equation

HRID 1502526 reaction equation
[C:1]([O:5]N1CCC(O)CC1=C=O)([CH3:4])([CH3:3])[CH3:2].[CH2:15]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])C.[C:22]([O:27][C:28](=O)C(C)=C)(=[O:26])[C:23]([CH3:25])=[CH2:24].[OH2:33]>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[C:22]([O:27][CH:28]1[CH2:21][CH2:20][N:17]([C:15]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:33])[CH2:18][CH2:19]1)(=[O:26])[C:23]([CH3:25])=[CH2:24]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 12974Methacrylic anhydrideHCID 86647632HCID 86647632, compound

Product 1

HCID 68648645HCID 68648645, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

In a nitrogen atmosphere, 50 g of 1-tert-butoxy-carbonylpiperidin-4-ol, 26.8 g of triethylamine, and 2.9 g of 4-dimethylaminopyridine were mixed in 200 g of toluene. Under ice cooling, 40 g of methacrylic anhydride was added dropwise to the solution at a temperature below 40° C. The solution was stirred for 4 hours at room temperature, whereupon 100 g of water was added dropwise below 20° C. to quench the reaction. This was followed by standard aqueous workup and vacuum distillation, obtaining 48.9 g of 1-tert-butoxycarbonylpiperidin-4-yl methacrylate (yield 90%).

Workup

  1. additionwas added dropwise below 20° C.
  2. customto quench
  3. customthe reaction
  4. distillationThis was followed by standard aqueous workup and vacuum distillation

Sources & evidence

ORD record
ord-2fa3c5bcaa9649f78d1d872014620f02
Source dataset
uspto-grants-2015_12
Patent number
US09207534B2

Reaction notes

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