Tetramethyl orthocarbonate → HCID 23725612, compound

HRID 1661433Notes

Reaction equation

HRID 1661433 reaction equation
Cl.[NH2:2][C:3]1[C:11]([OH:12])=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:5][CH:4]=1.[CH3:19][O:20][C:21](OC)(OC)OC>O1CCCC1.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH3:19][O:20][C:21]1[O:12][C:11]2[C:10]3[CH:9]([CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])[CH2:8][CH2:7][C:6]=3[CH:5]=[CH:4][C:3]=2[N:2]=1

Participants

6

Reactant 2

HCID 74613Tetramethyl orthocarbonateHCID 67354374N-[2-(6-Amino-7-hydroxy-2,3-dihydro-1H-inden-1-yl)ethyl]acetamide Hydrochloride

Product 1

HCID 23725612HCID 23725612, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

N-[2-(6-Amino-7-hydroxy-2,3-dihydro-1H-inden-1-yl)ethyl]acetamide hydrochloride (100 mg, 0.369 mmol) and tetramethoxymethane (151 mg, 1.11 mmol) were heated under reflux in tetrahydrofuran (3.7 mL) for 2 hr. The reaction solution was diluted with ethyl acetate and saturated aqueous sodium hydrogencarbonate solution, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→95/5) to give the title compound (58.4 mg, yield 58%).

Workup

  1. washwashed with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→95/5)

Sources & evidence

ORD record
ord-486b9302c3ab4c14890c5212207bc1f8
Source dataset
uspto-grants-2011_10
Patent number
US08030337B2

Reaction notes

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