Aluminium lithium hydride → HCID 58986359, compound

HRID 420799Notes

Reaction equation

HRID 420799 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([O:23][CH2:24][O:25][CH3:26])=[CH:20][CH:21]=2)[C:16]([C:27](OCC)=[O:28])=[C:15]1[CH:32]([CH3:34])[CH3:33])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N1C2C(=CC(OCOC)=CC=2)C(C(O)=O)=C1C(C)C)C1C=CC=CC=1>C1COCC1>[CH2:7]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([O:23][CH2:24][O:25][CH3:26])=[CH:20][CH:21]=2)[C:16]([CH2:27][OH:28])=[C:15]1[CH:32]([CH3:34])[CH3:33])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 58986361HCID 58986361, compoundHCID 66658644HCID 66658644, compound

Product 1

HCID 58986359HCID 58986359, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium aluminum hydride (LiAlH4, 144 mg, 3.6 mmol) in THF (10 ml) at 0° C. was added 1-benzyl-2-isopropyl-5-(methoxymethoxy)-1H-indole-3-carboxylic acid, ethyl ester (Compound 2, 270 mg, 0.71 mmol) in THF (5 ml) slowly. The reaction was stirred at room temperature for 4.5 h, cooled to 0° C., and it was quenched with H2O (0.7 ml) and 4 M NaOH (1.0 ml), Silica gel was added, and the mixture was diluted with EtOAc, and filtered through Celite, and it was concentrated to yield the crude product, (1-benzyl-2-isopropyl-5-(methoxymethoxy)-1H-indol-3-yl)methanol (Compound 3) as a clear oil, which was used immediately in the next step (Example 4) without further purification or characterization.

Workup

  1. temperaturecooled to 0° C.
  2. customit was quenched with H2O (0.7 ml) and 4 M NaOH (1.0 ml), Silica gel
  3. additionwas added
  4. additionthe mixture was diluted with EtOAc
  5. filtrationfiltered through Celite, and it
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-54abf050d8a5403d8f83d77951e3a746
Source dataset
uspto-grants-2012_01
Patent number
US08097644B2

Reaction notes

Loading…