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Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine → HCID 86679676, compound

HRID 577750
Notes
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Reaction equation

HRID 577750 reaction equation
[CH2:1]([N:8]([CH2:12][Si](C)(C)C)[CH2:9]OC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:17][CH:18]([F:24])/[CH:19]=[CH:20]/[N+:21]([O-:23])=[O:22]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH2:1]([N:8]1[CH2:12][C@@H:20]([N+:21]([O-:23])=[O:22])[C@H:19]([CH:18]([F:24])[F:17])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 86679677(1E)-3,3-difluoro-1-nitroprop-1-ene

Product 1

HCID 86679676HCID 86679676, compoundYield 48,780.801%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-benzyl-1-methoxy-N-((trimethylsilyl)methyl)methanamine (56.6 g, 0.24 mol) in dry CH2Cl2 (160 ml) was added (E)-3,3-difluoro-1-nitroprop-1-ene (25 g, 0.2 mmol) and a few drops of TFA at 0° C. The resulting mixture was stirred at rt overnight. The mixture was concentrated and purified by flash column chromatography (petroleum ether:EtOAc=100:1 to 25:1) to give the title compound (25 g, 49% yield) as a yellow oil.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by flash column chromatography (petroleum ether:EtOAc=100:1 to 25:1)

Sources & evidence

ORD record
ord-6835ac586640405882d15af12bec5e0f
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09040547B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes