Diethyl Ether → HCID 11187623, compound

HRID 494865Notes

Reaction equation

HRID 494865 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[C:20]([C:24](=[O:26])[CH3:25])[CH:21]=[CH:22][CH:23]=3)=[CH:14][C:12]=2[CH:13]=1.[CH3:27][Mg]Br.CCOCC>O1CCCC1>[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[C:20]([C:24]([OH:26])([CH3:27])[CH3:25])[CH:21]=[CH:22][CH:23]=3)=[CH:14][C:12]=2[CH:13]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 9884652HCID 9884652, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 11187623HCID 11187623, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 136C (87 mg, 0.25 mmol) was dissolved into tetrahydrofuran (5 mL), treated with 3 M methylmagnesium bromide in ether (0.3 mL, 0.9 mmol), stirred overnight, quenched with 0.5 M aqueous dipotassium hydrogen phosphate, and diluted with EtOAc and a little CH2Cl2. The resulting emulsion was sonicated, and the aqueous phase was separated and extracted with EtOAc. The combined organic phases were washed consecutively with 0.5 M aqueous dipotassium hydrogen phosphate and brine, dried (Na2SO4), concentrated, and chromatographed on silica with a gradient of 2 to 10% MeOH/20% MeCN/CH2Cl2 followed by 10% MeOH/CH2Cl2 to provide the title compound as an orange resin (˜33% yield). 1HNMR (300 MHz, CD3OD) δ 1.20 (d, 3H), 1.42-1.58 (m, 1H), 1.58 (s, 6H), 1.76-1.90 (m, 2H), 1.96-2.12 (m, 1H), 2.3-2.7 (m, 3H), 2.97-3.13 (m, 2H), 3.22-3.4 (m, 2H), 6.62 (s, 1H), 7.38 (dd, 1H), 7.40-7.46 (m, 2H), 7.46-7.48 (m, 2H), 7.72 (dd, 1H), 7.76 (dd, 1H).

Workup

  1. customquenched with 0.5 M aqueous dipotassium hydrogen phosphate
  2. additiondiluted with EtOAc
  3. customThe resulting emulsion was sonicated
  4. customthe aqueous phase was separated
  5. extractionextracted with EtOAc
  6. washThe combined organic phases were washed consecutively with 0.5 M aqueous dipotassium hydrogen phosphate and brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customchromatographed on silica with a gradient of 2 to 10% MeOH/20% MeCN/CH2Cl2

Sources & evidence

ORD record
ord-6f4ab93b83194ea1a9d510393ce34345
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Reaction notes

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