Triethylamine → 7-(tert-butylamino-methyl)-6-chloro-chroman-4(S)-ol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (1S,2S)-(+)-N-(4-toluene-sulfonyl)-1,2-diphenylethylenediamine (0.29 g, 8.08 mmol) in i-PrOH (15 mL) was added [RuCl2(n6-p-cymene)]2, and Et3N under argon. The mixture was heated at 80° C. for 1 h, cooled, and concentrated to dryness. To this mixture was added a solution of 7-(tert-butylamino-methyl)-6-chloro-chroman-4-one (12 g, 44.91 mole) in anhydrous CH3CN (150 mL), followed by 5:2 formic acid/TEA (6 mL). The reaction was stirred at RT for 24 h. The mixture was concentrated, taken up in H2O, neutralized with 10% Na2CO3, extracted with CH2Cl2 (3×), dried over MgSO4, concentrated to give a brown foam which was stirred in hexane/ether (1:1), and filtered. The filtrate was concentrated to give a light brown foam.

Provenance & Evidence