Tetrabutylammonium Fluoride → HCID 89660480, compound

HRID 2281006Notes

Reaction equation

HRID 2281006 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]1([C:28](=[O:36])[NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:18][CH2:17][CH2:16][N:15](C(OCC[Si](C)(C)C)=O)[CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([O:8][C:9](=[O:10])[NH:11][CH2:12][C:13]1([C:28](=[O:36])[NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 89648258HCID 89648258, compound

Product 1

HCID 89660480HCID 89660480, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction mixture of 2-(trimethylsilyl)ethyl 3-((((benzyloxy)carbonyl)amino)methyl)-3-(phenylcarbamoyl)piperidine-1-carboxylate (1200.00 mg; 2.35 mmol; 1.00 eq.) and TBAF (10.00 ml; 9.38 mmol; 4.00 eq.) in THF was stirred at RT overnight. The crude was purified by prep HPLC to afford the title compound (600 mg, 69.6%)

Workup

  1. customThe crude was purified by prep HPLC

Sources & evidence

ORD record
ord-6b900d14fbc1478abf3787c3021d7048
Source dataset
uspto-grants-2015_09
Patent number
US09139568B2

Reaction notes

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