Aluminium lithium hydride → HCID 66650190, compound

HRID 418555Notes

Reaction equation

HRID 418555 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([N:20]([C:31]2[CH:39]=[CH:38][C:34]3[S:35][CH:36]=[CH:37][C:33]=3[CH:32]=2)[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28](O)=[O:29])[CH:23]=2)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>C1COCC1>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([N:20]([C:31]2[CH:39]=[CH:38][C:34]3[S:35][CH:36]=[CH:37][C:33]=3[CH:32]=2)[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][OH:29])[CH:23]=2)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66650340HCID 66650340, compound

Product 1

HCID 66650190HCID 66650190, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium aluminum hydride (1.0 M, 0.24 mL, 0.24 mmol) was added at 0° C. to a solution of 4-[benzo[b]thiophen-5-yl-(3-carboxy-benzyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (55 mg, 0.12 mmol) in THF (2 mL). The reaction mixture was stirred for 1 hour and it was then quenched by addition of water, MeOH (1 drop) and an aqueous solution of KOH (15%, 2 drops). The resulting mixture was stirred for 15 minutes and it was filtered over a celite pad. The filtrate was evaporated under reduced pressure and the crude residue was purified by preparative TLC (6/4, hexane/EtOAc) to give 20 mg of 4-[benzo[b]thiophen-5-yl-(3-hydroxymethyl-benzyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester as a colorless oil. This material was dissolved in DCM (2 mL) and trifluoroacetic acid (100 μL) was added, the resulting mixture was stirred overnight. The solvent was evaporated under reduced pressure and the residue was triturated with Et2O to give 3 mg of 3-{[(1H-indol-5-yl)-piperidin-4-yl-amino]-methyl}-phenyl)-methanol trifluoroacetate as a gray powder.

Workup

  1. customit was then quenched by addition of water, MeOH (1 drop)
  2. stirringThe resulting mixture was stirred for 15 minutes
  3. filtrationit was filtered over a celite pad
  4. customThe filtrate was evaporated under reduced pressure
  5. customthe crude residue was purified by preparative TLC (6/4, hexane/EtOAc)

Sources & evidence

ORD record
ord-aeaeadd7f3cf41d48dd0eef122c35986
Source dataset
uspto-grants-2012_01
Patent number
US08093285B2

Reaction notes

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