Water → HCID 11264804, compound

Participants

Reaction Conditions

Reaction Steps

1-(4-Methoxy-benzyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (0.71 mmol) synthesized as described in example 12 is dissolved in 5 mL of anhydrous THF and cooled down to −78° C. A solution of freshly prepared LDA (0.85 mmol) is added to the mixture slowly. After stirring at the same temperature for 10 minutes, the mixture is allowed to warm up to 0° C. for 30 minutes and then cooled down to −78° C. again. Ethyl formate (3.55 mmol) is added dropwise to the reaction mixture. After the addition, the mixture is stirred at −78° C. for 10 minutes and then the temperature is risen to 0° C. for 1 hour. The reaction is quenched by addition of 1 mL of a mixture of water and EtOH (1:1), concentrated and dried under reduced pressure for 24 hours. The residue is redissolved in 4 mL of anhydrous THF, Na(AcO)3BH (2.1 mmol) is added to the mixture and the resulting mixture is stirred at room temperature for 16 hours. The reaction mixture is poured into 20 mL of water and extracted with EtOAc (3×10 mL). The organic layers are combined, washed with brine and dried over MgSO4. Solvent is removed under vacuum and the residue is purified by flash column chromatography (silica gel) to provide the desired product 3-hydroxymethyl-1-(4-methoxy-benzyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one as white solid. Yield: 45%. MS: (ES+): 312 [M+1].

Provenance & Evidence