Sodium Carbonate → HCID 54212612, compound

HRID 1683898Notes

Reaction equation

[CH2:1]([N:8]1[C@@H:17]2[C@H:12]([C:13]3[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]=O)[C:14]=3[CH2:15][CH2:16]2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:24]([CH2:27][C:28](OCC)=O)=[N+:25]=[N-:26].[CH3:33][O-].[Na+].[Cl-].[NH4+].[C:38](=[O:41])([O-])[O-:39].[Na+].[Na+]>CO.CCOCC>[CH3:33][O:39][C:38](=[O:41])[C:28]([CH2:27][N:24]=[N+:25]=[N-:26])=[CH:22][C:18]1[C:14]2[CH2:15][CH2:16][C@H:17]3[C@@H:12]([CH2:11][CH2:10][CH2:9][N:8]3[CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:13]=2[CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Trans-4-benzyl-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinolin-7-carbaldehyde (1.4 g, 4.59 mmol), ethyl azidoacetate (2.7g, 20.9 mmol), diethyl ether (10 ml), and methanol (30 ml) were cooled to -5° C. (Henn et al., J. Chem. Soc. Perkin Trans. I, 1984, 2189-2196). Sodium methoxide (3.89 ml, 18.4 mmol, of a 25% w/w solution in methanol) was slowly added. The reaction was allowed to reach ambient temperature and stirred for 1 hr. The mixture was cooled to 0° C. and saturated aqueous ammonium chloride added. The reaction was rapidly partioned between ether and 10% aqueous sodium carbonate. The ethereal layer was washed with water and brine and the resulting organic phase dried (magnesium sulfate) and evaporated to dryness. The residue was used without any further purifications (1.85 g, 100%).

Workup

customto reach ambient temperature
washThe ethereal layer was washed with water and brine
dry with materialthe resulting organic phase dried (magnesium sulfate)
customevaporated to dryness

Sources & evidence

ORD record: ord-83b1a04e50a04d42b507bbad690e2e79
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05639778

Reaction notes

Loading…