Aluminium lithium hydride → HCID 68917175, compound

HRID 870359Notes

Reaction equation

HRID 870359 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[O:20][CH2:19][CH:18]([NH:24][C:25](=O)[CH2:26][CH3:27])[CH2:17]3)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[O:20][CH2:19][CH:18]([NH:24][CH2:25][CH2:26][CH3:27])[CH2:17]3)(=[O:11])=[O:12])=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68920503HCID 68920503, compound

Product 1

HCID 68917175HCID 68917175, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-[6-(4-Isopropyl-benzenesulfonylamino)-chroman-3-yl]-propionamide (0.48 g, 1.20 mmol) was dissolved in THF (5 mL) and added dropwise to a stirred suspension of LiAlH4 (0.43 g, 11.3 mmol) in THF (5 mL) at 0° C. The resulting mixture was stirred at room temperature for 18 h. The solution was heated to reflux for 3 h, cooled and quenched by addition of water and 2 N HCl. The mixture was extracted with ethyl acetate and the organic phase dried over MgSO4, filtered, and the filtrate was evaporated in vacuo to give the product which was further purified by preparative HPLC (20-90% MeOH) to give a white solid (10 mg, 6%).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 3 h
  3. temperaturecooled
  4. customquenched by addition of water and 2 N HCl
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialthe organic phase dried over MgSO4
  7. filtrationfiltered
  8. customthe filtrate was evaporated in vacuo
  9. customto give the product which
  10. customwas further purified by preparative HPLC (20-90% MeOH)

Sources & evidence

ORD record
ord-debbb484911a4505a37cc2c9833e8a1b
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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