Tetrabutylammonium Fluoride → 1,1-Dimethylethyl {[3'-(hydroxymethyl)-5-(methyloxy)-3-biphenylyl]methyl}carbamate

HRID 662061Notes

Reaction equation

HRID 662061 reaction equation
CC([Si](C)(C)[O:6][CH2:7][C:8]1[CH:9]=[C:10]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:15]=2)[CH:11]=[CH:12][CH:13]=1)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:6][CH2:7][C:8]1[CH:9]=[C:10]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH:15]=2)[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 578132741,1-Dimethylethyl {[3'-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(methyloxy)-3-biphenylyl]methyl}carbamate

Product 1

HCID 578132931,1-Dimethylethyl {[3'-(hydroxymethyl)-5-(methyloxy)-3-biphenylyl]methyl}carbamateYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1,1-dimethylethyl {[3′-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(methyloxy)-3-biphenylyl]methyl}carbamate (1.5 g, 3.28 mmol) in THF (20 mL) was added a solution of nBu4NF (0.94 g, 3.61 mmol) in THF (10 mL). This mixture was stirred at room temperature over night. After the solvent was removed under reduced pressure, the residue was diluted with EtOAc (30 mL). The organic layer was washed with water (10 mL×2), brine (10 mL×2), and dried over Na2SO4. The product, 1,1-dimethylethyl {[3′-(hydroxymethyl)-5-(methyloxy)-3-biphenylyl]-methyl}carbamate, (0.9 g) was purified by flash column chomatography (PE:EA=3:1). (Yield: 80%). 1H NMR (400 MHz, CDCl3) δ 1.47 (s, 9H), 3.86 (s, 3H), 4.35 (d, J=7.6 Hz, 2H), 4.76 (s, 2H), 4.89 (s, 1H), 6.83 (s, 1H), 7.02 (s, 1H), 7.09 (s, 1H), 7.34-7.58 (m, 4H); 13C NMR (100 MHz, CDCl3) δ 28.4, 44.7, 55.4, 65.2, 79.6, 111.9, 118.7, 125.8, 126.1, 126.4, 129.0, 140.9, 141.2, 141.5, 142.8, 156.0, 160.3. HPLC: retention time: 11.558 min; purity: 98.7%; MS: m/z 343 (M+).

Workup

  1. customAfter the solvent was removed under reduced pressure
  2. additionthe residue was diluted with EtOAc (30 mL)
  3. washThe organic layer was washed with water (10 mL×2), brine (10 mL×2)
  4. dry with materialdried over Na2SO4
  5. customThe product, 1,1-dimethylethyl {[3′-(hydroxymethyl)-5-(methyloxy)-3-biphenylyl]-methyl}carbamate, (0.9 g) was purified by flash column chomatography (PE:EA=3:1)

Sources & evidence

ORD record
ord-cfd26759103a40dd91645701fce8fffa
Source dataset
uspto-grants-2011_12
Patent number
US08084449B2

Reaction notes

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