Water → HCID 23114226, compound

HRID 1787328Notes

Reaction equation

HRID 1787328 reaction equation
[CH3:1][C:2]([CH3:36])([CH3:35])[CH2:3][C:4]([NH:6][C:7]1[C:8]([CH3:34])=[C:9]([CH3:33])[C:10]2[O:14][CH2:13][CH:12]([C:15]3[CH:16]=[CH:17][C:18]([CH:28]([CH3:30])[CH3:29])=[C:19]([CH:27]=3)[O:20][CH2:21][C:22](OCC)=[O:23])[C:11]=2[C:31]=1[CH3:32])=[O:5].[Li].O>C1COCC1>[OH:23][CH2:22][CH2:21][O:20][C:19]1[CH:27]=[C:15]([CH:12]2[C:11]3[C:31]([CH3:32])=[C:7]([NH:6][C:4](=[O:5])[CH2:3][C:2]([CH3:36])([CH3:35])[CH3:1])[C:8]([CH3:34])=[C:9]([CH3:33])[C:10]=3[O:14][CH2:13]2)[CH:16]=[CH:17][C:18]=1[CH:28]([CH3:29])[CH3:30]

Participants

5

Reactant 3

HCID 962WaterHCID 3028194LithiumHCID 86612360HCID 86612360, compound

Product 1

HCID 23114226HCID 23114226, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (5-(5-((3,3-dimethylbutanoyl)amino)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-3-yl)-2-isopropylphenoxy)acetate (200 mg, 0.49 mmol) obtained in Example 188 in THF (5 mL) was added with ice-cooling lithium borotetrahydride (43 mg, 2.00 mmol). The reaction solution was warmed to room temperature and stirred for 60 hours. The reaction solution was added to ice and water was added to the reaction solution, and the product was extracted with ethyl acetate. The combined organic layers were washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 157 mg (yield: 71%) of the title compound. Melting point: 155-156° C. (ethyl acetate-hexane).

Workup

  1. additionwas added to the reaction solution
  2. extractionthe product was extracted with ethyl acetate
  3. washThe combined organic layers were washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cfaa8c2e44be4996be35a4e3f9a95f33
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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