Aluminium lithium hydride → N-(2-chlorophenyl)-8-(hydroxymethyl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

HRID 84499Notes

Reaction equation

HRID 84499 reaction equation
C[O:2][C:3]([C:5]1[CH:29]=[CH:28][C:8]2[C:9]3[S:10][C:11]([C:17](=[O:27])[N:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[Cl:26])[CH3:19])=[CH:12][C:13]=3[CH2:14][CH2:15][O:16][C:7]=2[CH:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[N:18]([CH3:19])[C:17]([C:11]1[S:10][C:9]2[C:8]3[CH:28]=[CH:29][C:5]([CH2:3][OH:2])=[CH:6][C:7]=3[O:16][CH2:15][CH2:14][C:13]=2[CH:12]=1)=[O:27]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 442423632-[(2-Chloro-phenyl)-methyl-carbamoyl]-4,5-dihydro-6-oxa-1-thia-benzo[e]azulene-8-carboxylic acid methyl ester

Product 1

HCID 44242781N-(2-chlorophenyl)-8-(hydroxymethyl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamideYield 48.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[(2-chloro-phenyl)-methyl-carbamoyl]-4,5-dihydro-6-oxa-1-thia-benzo[e]azulene-8-carboxylic acid methyl ester (1 g, 2.3 mmol) in dry THF (30 mL) was added lithium aluminum hydride (174 mg, 4.6 mmol) by portion at 0° C. The resulting mixture was stirred under nitrogen atmosphere for 30 minutes. The reaction was monitored by LC-MS. When the starting material was disappeared, the reaction mixture was quenched by the slow addition of water and 10% NaOH aqueous solution. After filtered, the filtrate was concentrated to the crude product, which was recrystallized from MeOH to give 190 as a yellow solid (450 mg, yield 48.9%). MS (ESI) 399.8

Workup

  1. customthe reaction mixture was quenched by the slow addition of water and 10% NaOH aqueous solution
  2. filtrationAfter filtered
  3. concentrationthe filtrate was concentrated to the crude product, which
  4. customwas recrystallized from MeOH

Sources & evidence

ORD record
ord-66db130c158440d8ad84fc4cf9a0bc32
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

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