Formaldehyde → HCID 86640761, compound

Participants

Reaction Steps

A solution of the cis/trans mixture of decahydroquinoline diastereomers (1.20 g, 3.48 mmol), formaldehyde (1.1 mL, 13.9 mmol) as a 37 wt % solution in H2O, trimethylsilyl acetylene (963 μL, 6.95 mmol), and AuBr3 (455 mg, 1.04 mmol) in H2O (2.0 mL) was heated at 75° C. overnight. LC/MS of an aliquot showed the reaction had not gone to completion. The reaction mixture was charged with a second portion of formaldehyde (1.1 mL, 13.9 mmol) as a 37 wt % solution in H2O and trimethylsilyl acetylene (963 μL, 6.95 mmol) and heated at 75° C. for an additional 72 hr. The reaction mixture was diluted with EtOAc and filtered through a Celite pad, washing with EtOAc (25 mL). The solution was concentrated and purified by chromatography, eluting with 0-20% EtOAc/hexanes to give 413 mg (26%) of the cis-decahydroquinoline trimethylsilyl acetylene as a colorless oil confirmed by MS (ESI+): cal'd [M+H]+ 466.6, exp. 466.1.

Provenance & Evidence