Tetrabutylammonium Fluoride → 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-hydroxymethyl-3-methylpyridin

HRID 1789826Notes

Reaction equation

HRID 1789826 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:23][C:24]([N:26]([C:34]1[C:39]([CH3:40])=[CH:38][C:37]([C:41](C)(C)[O:42][SiH2]C(C)(C)C)=[CH:36][N:35]=1)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:25])([CH3:22])([CH3:21])[CH3:20]>C1COCC1>[C:19]([O:23][C:24]([N:26]([C:34]1[C:39]([CH3:40])=[CH:38][C:37]([CH2:41][OH:42])=[CH:36][N:35]=1)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:25])([CH3:20])([CH3:21])[CH3:22]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 1317258272-[N,N-bis(tert-butoxycarbonyl)amino]-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-methylpyridin

Product 1

HCID 220360372-[N,N-bis(tert-butoxycarbonyl)amino]-5-hydroxymethyl-3-methylpyridinYield 59.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (25.1 g 79.6 mmol) was added to a solution of 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-methylpyridin (18.0 g, 39.8 mmol) in THF (150 mL). The reaction mixture was stirred overnight at room temperature. Concentration under reduced pressure followed by flash chromatography (hexane/EtOAc, 50:50) gave 2-[N,N -bis(tert-butoxycarbonyl)amino]-5-hydroxymethyl-3-methylpyridin (8.0 g, 59%).

Workup

  1. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-7f016dac5a71499cab1442bd665fa2a5
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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