Tetrabutylammonium Fluoride → 1,1-Dimethylethyl {[3'-(hydroxymethyl)-4-methyl-3-biphenylyl]methyl}carbamate

HRID 662059Notes

Reaction equation

HRID 662059 reaction equation
CC([Si](C)(C)[O:6][CH2:7][C:8]1[CH:9]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[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]=[CH:18][C:17]([CH3:20])=[C:16]([CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[CH:15]=2)[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 578134201,1-Dimethylethyl {[3'-({[(1,1-dimethylethyl)(dimethyl)silyl]-oxy}methyl)-4-methyl-3-biphenylyl]methyl}carbamate

Product 1

HCID 578134391,1-Dimethylethyl {[3'-(hydroxymethyl)-4-methyl-3-biphenylyl]methyl}carbamateYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1,1-dimethylethyl {[3′-({[(1,1-dimethylethyl)(dimethyl)silyl]-oxy}methyl)-4-methyl-3-biphenylyl]methyl}carbamate (3.60 g, 8.2 mmol) in THF (30 mL), was added a solution of nBu4NF (2.34 g, 9.0 mmol) in THF (20 mL). This mixture was stirred at room temperature over night. The solvent was removed under reduced pressure, and the residue was diluted with CH2Cl2 (50 mL), washed with water (15 mL×2), brine (15 mL×2), and dried over Na2SO4. The product 1,1-dimethylethyl {[3′-(hydroxymethyl)-4-methyl-3-biphenylyl]methyl}carbamate (1.5 g) was purified by flash column chomatography (PE:EA=4:1) (yield: 53%). 1H NMR (400 MHz, CDCl3) δ 1.47 (s, 9H), 2.37 (s, 3H), 4.37 (d, J=5.6 Hz, 2H), 4.76 (m, 3H), 7.23-7.58 (m, 7H); 13C NMR (100 MHz, CDCl3) δ 18.6, 28.4, 42.9, 65.3, 79.5, 125.6, 125.7, 126.2, 126.8, 129.0, 130.9, 135.5, 138.9, 141.2, 141.4, 155.8; HPLC: retention time: 14.965 min; purity: 95.4%; MS m/z 327 (M+).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with CH2Cl2 (50 mL)
  3. washwashed with water (15 mL×2), brine (15 mL×2)
  4. dry with materialdried over Na2SO4
  5. customThe product 1,1-dimethylethyl {[3′-(hydroxymethyl)-4-methyl-3-biphenylyl]methyl}carbamate (1.5 g) was purified by flash column chomatography (PE:EA=4:1) (yield: 53%)

Sources & evidence

ORD record
ord-6017290adc0c4f7f9fbd09bf4ee1c644
Source dataset
uspto-grants-2011_12
Patent number
US08084449B2

Reaction notes

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