Aluminium lithium hydride → HCID 59331548, compound

HRID 1881974Notes

Reaction equation

HRID 1881974 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[N:31]=[CH:30][C:29]([CH:32]([C:38](OCC)=[O:39])[C:33](OCC)=[O:34])=[CH:28][CH:27]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[N:31]=[CH:30][C:29]([CH:32]([CH2:33][OH:34])[CH2:38][OH:39])=[CH:28][CH:27]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:11][CH:12]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 59331373HCID 59331373, compound

Product 1

HCID 59331548HCID 59331548, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of diethyl [6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]malonate (100 mg) in tetrahydrofuran (1.5 mL) was added to a suspension of lithium aluminum hydride (15 mg) in tetrahydrofuran (1.5 mL) under ice-cooling, and the mixture was stirred for 2 hr. Lithium aluminum hydride (30 mg) was further added, and the mixture was stirred with heating under reflux overnight. After cooling to room temperature, the reaction mixture was diluted with tetrahydrofuran, and the reaction was quenched with sodium sulfate decahydrate. The reaction mixture was filtered through celite, and the filtrate was concentrated. The residue was subjected to preparative HPLC to give the title compound (15 mg, yield 15%) as a yellow amorphous solid. MS: 511 (MH+).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred
  3. temperaturewith heating
  4. temperatureunder reflux overnight
  5. customthe reaction was quenched with sodium sulfate decahydrate
  6. filtrationThe reaction mixture was filtered through celite
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-455b55dc3acc46de8b62019dcd269c91
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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