Tetrabutylammonium Fluoride → 3-(2-Cyclohexylcarbamoyloxymethyl-4-hydroxyphenyl)propionic acid tert-butyl ester

HRID 1181116Notes

Reaction equation

HRID 1181116 reaction equation
[C:1]([O:5][C:6](=[O:44])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:11][C:10]=1[CH2:33][O:34][C:35](=[O:43])[NH:36][CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([O:5][C:6](=[O:44])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH2:33][O:34][C:35](=[O:43])[NH:36][CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 589793663-[4-(tert-Butyldiphenylsilanyloxy)-2-cyclohexylcarbamoyloxymethylphenyl]propionic acid tert-butyl ester

Product 1

HCID 589789753-(2-Cyclohexylcarbamoyloxymethyl-4-hydroxyphenyl)propionic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 500 mL round bottomed flask was charged with 3-[4-(tert-butyldiphenylsilanyloxy)-2-cyclohexylcarbamoyloxymethylphenyl]propionic acid tert-butyl ester (3.1 g, 5.03 mmol) and anhydrous THF (180 mL). Tetrabutylammonium fluoride (15.1 mL, 15.1 mmol, 1.0M in THF) was added, and the reaction mixture was stirred at ambient temperature under a nitrogen atmosphere for 4 h. The mixture was concentrated, and the residue was diluted with EtOAc (100 mL), washed with brine, dried over (Na2SO4), and concentrated to give an oil. This crude oil was purified using the Biotage medium pressure chromatography system (EtOAc:hexanes 10:90 to 50:50) to a colorless oil (1.67 g, 88%). 1H NMR (400 MHz, CDCl3) δ 1.04-1.19 (m, 3H), 1.24-1.38 (m, 2H), 1.42 (s, 9H), 1.57-1.62 (m, 1H), 1.66-1.71 (m, 2H), 1.91-2.05 (m, 2H), 2.47 (t, J=7.8 Hz, 2H), 2.88 (t, J=7.8 Hz, 2H), 3.48-3.50 (m, 1H), 4.77-4.78 (m, 1H), 5.07 (s, 2H), 5.40 (s, 1H), 6.73 (dd, J=8.3, 2.9 Hz, 1H), 6.84 (d, J=2.4 Hz, 1H), 7.07 (d, J=8.3 Hz, 1H). MS (ES) m/e 378 (M+1).

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was diluted with EtOAc (100 mL)
  3. washwashed with brine
  4. dry with materialdried over (Na2SO4)
  5. concentrationconcentrated
  6. customto give an oil
  7. customThis crude oil was purified

Sources & evidence

ORD record
ord-0d20b9c2de2642f99f2762ad9f1ddf32
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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