Tetrabutylammonium Fluoride → tert-Butyl (4-(hydroxymethyl)-2-methoxyphenyl)carbamate

HRID 576451Notes

Reaction equation

HRID 576451 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[C:12]([O:24][CH3:25])[CH:11]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[C:12]([O:24][CH3:25])[CH:11]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86720227Tert-butyl 4-((tert-butyldimethylsilyloxy) methyl)-2-methoxyphenylcarbamate

Product 1

HCID 86720230tert-Butyl (4-(hydroxymethyl)-2-methoxyphenyl)carbamateYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of protected alcohol 7 (242.4 mg, 0.66 mmol) in THF (2.5 ml) was added a solution of 1M tetrabutylammonium fluoride in THF (0.73 ml, 0.73 mmol) and the mixture was stirred at room temperature for 24 hrs. The crude product was adsorbed on silica gel and purified by MPLC, eluting with hexanes/ethyl acetate 40%-50% gradient to give the title alcohol (92.9 mg, 56% yield). H-NMR (400 MHz, CD2Cl2): 8.85 (1H, brs) 7.78 (1H, d, J=8 Hz) 7.09 (1H, s) 6.82 (1H, dd, J=8 Hz, 0.4 Hz) 4.58 (2H, d, J=4 Hz) 3.5 (1H, t, J=4 Hz) 1.18 (9H, s).

Workup

  1. custompurified by MPLC
  2. washeluting with hexanes/ethyl acetate 40%-50% gradient

Sources & evidence

ORD record
ord-f03a0dac32984d3c9e7b632b53d8c3cb
Source dataset
uspto-grants-2015_05
Patent number
US09040019B2

Reaction notes

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