Triethylamine → 3-Dipropylamino-5-methyloxycarbonylchroman
Reaction equation
[CH2:1]([N:4]([CH2:22][CH2:23][CH3:24])[CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2S(C(F)(F)F)(=O)=O)[O:7][CH2:6]1)[CH2:2][CH3:3].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.CN(C)[CH:63]=[O:64].[CH3:66][OH:67]>C1(C)C=CC=CC=1>[CH2:1]([N:4]([CH2:22][CH2:23][CH3:24])[CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[C:66]([O:64][CH3:63])=[O:67])[O:7][CH2:6]1)[CH2:2][CH3:3]Participants
6
Conditions
- Temperature
- 70 °C
Procedure
3-Dipropylamino-5-trifluoromethanesulfonylchroman (Example 1; 4.43 g, 11.6 mmol) was dissolved in 80 mL dimethylformamide/methanol 6:2 and the solution was degassed (10 mm Hg, 20° C., 15 min). PdOAc2 (76 mg, 0.34 mmol), 1,3-bis-diphenylphosphinopropane (141 mg, 0.34 mmol) and triethylamine (3.5 mL, 25 mmol) were then added. The mixture was heated to 70° C. under CO atmosphere and stirred for 5 hours. The solution was cooled, diluted with toluene (200 mL), washed with aqueous NaHCO3, dried with Na2SO4 and evaporated to dryness. The oil was purified by flash chromatography (silica gel) by elution with ethyl acetate/hexane 1:8. Yield: 76%, Mp 150°-152° C. (HCl-salt).
Workup
- customthe solution was degassed (10 mm Hg, 20° C., 15 min)
- temperatureThe solution was cooled
- washwashed with aqueous NaHCO3
- dry with materialdried with Na2SO4
- customevaporated to dryness
- customThe oil was purified by flash chromatography (silica gel) by elution with ethyl acetate/hexane 1:8
Sources & evidence
- ORD record
- ord-0595e6bda57d4d278a420e53759717b1
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05420151
Reaction notes
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