Trimethyl orthoformate → HCID 67551008, compound

HRID 987093Notes

Reaction equation

HRID 987093 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([CH2:11]C=O)[N:6]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])=[O:4].[CH:24]([O:29][CH3:30])([O:27][CH3:28])OC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([CH2:11][CH:24]([O:27][CH3:28])[O:29][CH3:30])[N:6]1[C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15])=[O:4]

Participants

5

Reactant 4

HCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 54416234HCID 54416234, compound2×

Product 1

HCID 67551008HCID 67551008, compoundYield 96%

Procedure

6-(2-Oxo-ethyl)-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (Compound 236, 0.4 g, 1.25 mmol), trimethyl orthoformate (5 mL) and p-toluenesulfonic acid monohydrate (0.03 g) were combined, and the reaction mixture was stirred at room temperature for 12 hours. Aqueous NaHCO3 (25 mL) was added and the reaction was extracted with CHCl3 (3×100 mL). The combined organic layer was dried over MgSO4 and concentrated. The residue was purified by flash chromatography (1:2 EtOAc/hexanes) to afford Compound 237 (0.441 g, 96%). Rf=0.75 (1:1 EtOAc/hexanes).

Workup

  1. extractionthe reaction was extracted with CHCl3 (3×100 mL)
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography (1:2 EtOAc/hexanes)

Sources & evidence

ORD record
ord-eebf216e20864f699bf24e99ceb57f5c
Source dataset
uspto-grants-2003_10
Patent number
US06630472B1

Reaction notes

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