Acetic Acid → HCID 67315625, compound

Participants

Reaction Steps

To a solution of (R)-1-benzyl-pyrrolidin-3-ylamine (1.0 g, 6 mmol), tetrahydro-4H-pyran-4-one (0.6 g, 6 mmol) in CH2Cl2 (15 ml) was added acetic acid (0.7 ml, 11 mmol) and sodium triacetoxyborohydride (1.4 g, 7 mmol) and the reaction stirred for 1 h. EtOH (15 ml) was added to the reaction, followed by formaldehyde (1 ml, 36% solution in water) and finally sodium cyanoborohydride (0.4 g, 7 mmol) and the reaction stirred for a further 15 minutes. The reaction was then concentrated, the residue redissolved in CH2Cl2, washed with saturated NaHCO3, dried (Na2SO4) and concentrated. Purification by flash column chromatography (CH2Cl2:MeOH 9:1) afforded the title product (0.7 g, 44%) as a brown oil. MS: 275.2 (MH+).

Provenance & Evidence