Propionic Acid → HCID 14576241, compound

HRID 232150Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[C:12]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[N:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+].B(F)(F)F.[CH3:33]COCC.C(O)(=O)CC>C1COCC1>[CH3:33][O:25][C:24](=[O:26])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][C:12]1[C:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:18]=2[N:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[N:11]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 6-[4,5,6,7-tetrahydro-1-(4-nitrophenyl)-1H-inda-zol-3-yl]hexanoic acid (1.11 g, 3 mmol) in THF (10 ml) was treated with sodium borohydride (0.175 g) and boron trifluoride etherate (4.7 mmol) in THF (11 ml) during 0.5 hour. The solution was reacted for 18 hours at ambient temperature, treated with propionic acid (2 ml), and heated at 70° C. for 2 hours. The solution was cooled, dilution with water and the precipitate was extracted into ethyl acetate. Drying and evaporation of solvent gave crude title compound (1.69 g) as a viscous residue. Polar impurities were removed by filtration through silica gel (100 g) to yield pure title compound (0.45 g), m.p. 60°-61° C., after methanol crystallization.

Workup

customThe solution was reacted for 18 hours at ambient temperature
temperatureThe solution was cooled
extractiondilution with water and the precipitate was extracted into ethyl acetate
customDrying
customevaporation of solvent
customgave crude title compound (1.69 g) as a viscous residue
customPolar impurities were removed by filtration through silica gel (100 g)

Sources & evidence

ORD record: ord-214b336196304f2e93dc895680d62fc2
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04851425

Reaction notes

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