Cesium carbonate → HCID 59300500, compound

HRID 2235908Notes

Reaction equation

HRID 2235908 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C@H:7]([C@H:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13])[CH2:6][CH2:5]2.Br[C:18]([Br:21])([CH3:20])C.[C:22]([O-])([O-])=O.[Cs+].[Cs+]>O.CN(C=O)C>[Br:21][CH2:18][CH2:20][CH2:22][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C@H:7]([C@H:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13])[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 116582,2-DibromopropaneHCID 60128070HCID 60128070, compound

Product 1

HCID 59300500HCID 59300500, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6228DimethylformamideSolvent

Procedure

Methyl (2S)-2-[(1S)-5-hydroxy-2,3-dihydro-1H-inden-1 yl]propanoate (Example 14) (500 mg, 2.27 mmol), dibromopropane (4.308 g, 21.34 mmol), Cs2CO3 (834 mg, 2.56 mmol), and water (5 drops) were combined in DMF (20 mL) and stirred for 7 h at rt. The reaction mixture was concentrated under reduced pressure, water was added and the aqueous solution was extracted with EtOAc (2×). The combined organic phases were dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by silica gel flash chromatography (EtOAc/hexane (v/v)=1:25) gave 263 mg (34%) of the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 1.08 (d, 3H), 1.91 (m, 1H), 2.17 (m, 1H), 2.32 (m, 2H), 2.80 (m, 1H), 2.88 (m, 2H), 3.51 (m, 1H), 3.61 (t, 2H), 3.72 (s, 3H), 4.08 (t, 2H), 6.69 (d, 1H), 6.76 (s, 1H), 6.98 (d, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water
  2. additionwas added
  3. extractionthe aqueous solution was extracted with EtOAc (2×)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by silica gel flash chromatography (EtOAc/hexane (v/v)=1:25)

Sources & evidence

ORD record
ord-9206c31e495e40198c626776f18ebc3a
Source dataset
uspto-grants-2010_05
Patent number
US07714004B2

Reaction notes

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