Tetrabutylammonium Fluoride → HCID 11954559, compound

HRID 1626305Notes

Reaction equation

HRID 1626305 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][CH2:27][CH2:28][CH2:29][N:30]([CH3:41])[C:31](=[O:40])[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(C(C)(C)C)(C)C>C1COCC1>[OH:26][CH2:27][CH2:28][CH2:29][N:30]([CH3:41])[C:31](=[O:40])[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58358782HCID 58358782, compound

Product 1

HCID 11954559HCID 11954559, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (12.8 ml, 1.0 M solution in THF, 12.8 mmol) was added to the solution of benzyl 3-(tert-butyldimethylsilyloxy)propyl(methyl)carbamate obtained in step 3 (3.6 g, 10.7 mmol) in THF (30 ml). After reaction complete, water and EtOAC work-up and then drying were followed to give benzyl 3-hydroxypropyl(methyl)carbamate (formula 31). After further purification, alcohol was treated with triphenylphosphine (3.35 g, 12.8 mmol) and carbon tetrabromide (12.8 mmol) in acetonitrile (20 ml). The reaction progress was monitored by TLC or LS/MS. After reaction complete, the organic layer was extracted and evaporated. The residue was purified with silica gel column chromatography (EtOAC:Hx=1:5) to give the title compound (2.5 g, 82%, 2 steps) as light yellow oil.

Workup

  1. customAfter reaction complete
  2. dry with materialwater and EtOAC work-up and then drying

Sources & evidence

ORD record
ord-87d04f42bf9648b99d2096ec2f0d19ba
Source dataset
uspto-grants-2014_07
Patent number
US08785453B2

Reaction notes

Loading…