Water → HCID 21460517, compound

HRID 1941247Notes

Reaction equation

HRID 1941247 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([N:16]2[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:25])[CH2:12][C:13](O)=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].B.O.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([N:16]2[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:25])[CH2:12][CH2:13][OH:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6331BoraneHCID 11430Potassium CarbonateHCID 35695923-(3,4-dimethoxyphenyl)-3-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)propanoic acid

Product 1

HCID 21460517HCID 21460517, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of 3-(3',4'-dimethoxyphenyl)-3-(1'-oxoisoindolinyl)propionic acid (3.74 grams, 10.96 mmol) in THF (60 mL) at -10°-15° C. (ice-salt bath), was added borane in THF (11 mL, 1M, 11 mmol). The suspension was allowed to warm to room temperature slowly overnight. To the resulting clear solution was added water (20 mL), followed by potassium carbonate (6 g). The organic layer was separated. The aqueous layer was extracted with methylene chloride (2×50 mL). The combined organic layers were washed with sodium carbonate (20 mL, sat), brine (20 mL), and dried over magnesium sulfate. Removal of solvent and chromatography (silica gel, 100 grams, 1:2, 1:1 EtOAc/CH2Cl2) gave 3-(3',4'-dimethoxyphenyl)-3-(1'-oxoisoindolinyl)-1-propanol as an oil, (2.52 grams, 70%). Ether (6 mL) and 2 drops of methanol were added to the oil. Hexane was added until the solution was turned cloudy. The mixture was stirred for 30 minutes to give a white solid and the solid was filtered: mp, 101.5°-103.0° C.; 1H NMR (CDCl3)δ1.99-2.36 (m, 3H, CH2, OH), 3.49-3.80 (m, 2H, OCH2), 3.85 (s, 3H, CH3), 3.89 (s, 3H, CH3), 3.91 (d, J=17.2 Hz, 1H, CHH), 4.19 (d, J=17.2 Hz, 1H, CHH), 5.75 (dd, J=4, 11.5 Hz, 1H, NCH), 6.86-7.00(m, 3H, Ar), 7.27-7.56 (m, 3H, Ar), 7.86-7.89 (m, 1H, Ar); 13C NMR (CDCl3)δ33.87, 46.22, 50.61, 55.91, 56.01, 58.55, 111.04, 111.73, 119.66, 122.81, 123.89, 128.64, 131.33, 131.56, 132.09, 141.35, 148.81, 148.24, 169.45; Anal Calcd for C19H21 NO4 : C, 69.71; H, 6.47; N, 4.28. Found: C, 69.5I; H, 6.27; N, 4.12.

Workup

  1. customThe organic layer was separated
  2. extractionThe aqueous layer was extracted with methylene chloride (2×50 mL)
  3. washThe combined organic layers were washed with sodium carbonate (20 mL, sat), brine (20 mL)
  4. dry with materialdried over magnesium sulfate
  5. customRemoval of solvent and chromatography (silica gel, 100 grams, 1:2, 1:1 EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-c7ea2c0a67874b60af295a59cff7b7d1
Source dataset
uspto-grants-1997_12
Patent number
US05703098

Reaction notes

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