Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine → HCID 86679679, compound

HRID 928205Notes

Reaction equation

HRID 928205 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:9])[NH:5][C:6](=[O:8])[CH:7]=1.CO[CH2:12][N:13]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:14][Si](C)(C)C>C(Cl)Cl.C(=O)(O)[O-].[Na+].C(O)(C(F)(F)F)=O>[CH2:19]([N:13]1[CH2:14][C@:3]2([O:2][CH3:1])[C:4](=[O:9])[NH:5][C:6](=[O:8])[C@@H:7]2[CH2:12]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 2

HCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 116726673-methoxy-1H-Pyrrole-2,5-dione

Product 1

HCID 86679679HCID 86679679, compoundYield 288.1%

Reagents, catalysts & solvents 3

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 3-methoxy-1H-pyrrole-2,5-dione (3 g, 24 mmol) and TFA (0.34 g, 3 mmol) in CH2Cl2 (300 mL) was added slowly a solution of N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (14.2 g, 48 mmol) in CH2Cl2 (100 mL) at a rate such to maintain the internal reaction temperature <2° C. The resulting solution was slowly warmed to ambient temperature and stirred overnight. TLC (petroleum ether/EtOAc=1/1) showed the reaction was complete. The combined five batches of reaction mixture was diluted with saturated sodium bicarbonate (100 mL), and the organics was dried over MgSO4, concentrated and purified by column chromatography (from petroleum ether/EtOAc=10/1 to petroleum ether/EtOAc=1/1) to afford title product (18 g, for 5 batches, 58% yield) as a light yellow oil, which was further purified by preparative HPLC to afford pure title product (4.5 g, 14.6% yield) as an oil.

Workup

  1. temperatureto maintain the internal reaction temperature <2° C
  2. customfive batches of reaction mixture
  3. dry with materialthe organics was dried over MgSO4
  4. concentrationconcentrated
  5. custompurified by column chromatography (from petroleum ether/EtOAc=10/1 to petroleum ether/EtOAc=1/1)

Sources & evidence

ORD record
ord-c4352f00b33145d78a84afada0542daa
Source dataset
uspto-grants-2016_03
Patent number
US09290496B2

Reaction notes

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