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

HRID 564481Notes

Reaction equation

HRID 564481 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), the solution of nBu4NF (0.94 g, 3.61 mmol) in THF (10 mL) was added, and then the 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 chromatography (PE:EA=3:1). (Yield: 80%). 1H NMR (400 MHz, CDCl3): δ 1.47 (s, 9 H), 3.86 (s, 3 H), 4.35 (d, J=7.6 Hz, 2 H), 4.76 (s, 2 H), 4.89 (s, 1 H), 6.83 (s, 1 H), 7.02 (s, 1 H), 7.09 (s, 1 H), 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 chromatography (PE:EA=3:1)

Sources & evidence

ORD record
ord-5905e7e506324275b32124d2013db2d4
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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