Di-tert-butyl dicarbonate → Fluorene

HRID 2369470Notes

Reaction equation

HRID 2369470 reaction equation
CNC[C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>>[CH:9]1[C:8]2[CH2:7][C:6]3[C:14](=[CH:15][CH:16]=[CH:4][CH:5]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 126897512-((Methylamino)methyl)fluorene

Product 1

HCID 6853Fluorene

Procedure

A solution of fluorene-2-carbonyl chloride (prepared from fluorene-2-carboxylic acid and oxalyl chloride) in THF is added to aqueous methylamine (2 molar equivalents) to prepare N-methyl fluorene-2-carboxamide. Reduction of the amide using LiAlH4 in ether provides 2-((methylamino)methyl)fluorene. The amine is protected by reaction with di-tert-butyl dicarbonate to provide 24N-tBOC—N-methylamino)methyl)fluorene.

Sources & evidence

ORD record
ord-efd9463f124d49fa8ff9c5cccd6483d0
Source dataset
uspto-grants-2014_04
Patent number
US08703907B2

Reaction notes

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