Tetrabutylammonium Fluoride → HCID 67134124, compound

HRID 17962Notes

Reaction equation

HRID 17962 reaction equation
[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([N:23]3[CH2:27][CH2:26][CH2:25][CH:24]3[C:28](C)(C)[O:29][SiH2]C(C)(C)C)(=[O:22])=[O:21])=[CH:16][CH:15]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([N:23]3[CH2:27][CH2:26][CH2:25][CH:24]3[CH2:28][OH:29])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131727880HCID 131727880, compound

Product 1

HCID 67134124HCID 67134124, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of crude (6-{4-[2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidine-1-sulfonyl]phenyl}-pyridin-2-yl)carbamic acid tert-butyl ester (22.2 g, 40.5 mmol) and TBAF (21.2 g, 81.0 mmol) in DCM (300 mL) was stirred at room temperature overnight. The mixture was washed with brine (100 mL×3), dried over Na2SO4 and evaporated under vacuum to give {6-[4-(2-hydroxymethyl-pyrrolidine-1-sulfonyl)-phenyl]pyridin-2-yl}carbamic acid tert-butyl ester (15.0 g, 86%), which was used directly in the next step.

Workup

  1. washThe mixture was washed with brine (100 mL×3)
  2. dry with materialdried over Na2SO4
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-0131982467494261a64571b57cc0396a
Source dataset
uspto-grants-2010_06
Patent number
US07741321B2

Reaction notes

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