Triethylamine → HCID 86680654, compound

HRID 1615413Notes

Reaction equation

HRID 1615413 reaction equation
CCN(CC)CC.I[C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]2[CH2:20][O:19][CH2:18][CH2:17][N:16]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:11][CH:10]=1>CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:24][O:23][C:21]([C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]2[CH2:20][O:19][CH2:18][CH2:17][N:16]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:11][CH:10]=1)=[O:22]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 86680653HCID 86680653, compound

Product 1

HCID 86680654HCID 86680654, compoundYield 321.2%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Carbon monoxide gas was bubbled through a reaction mixture containing Et3N (4.742 g, 6.532 ml, 48.86 mmol), tert-butyl (3R)-3-(4-iodophenyl)morpholine-4-carboxylate 8 (5.21 g, 13.39 mmol) and Pd(dppf)Cl2—CH2Cl2 (1.093 g, 1.339 mmol) in methanol (157 mL) cooled in an ice bath for 10 mins. The reaction vessel was quickly sealed and the reaction mixture heated at 65° C. for 18 h. The reaction mixture cooled to rt and filtered through celite, washing through with methanol. The filtrate was concentrated in vacuo and crude product purified by ISCO companion (330 g SiO2 0 to 20% EtOAc/petroleum ether) and the product fractions combined and concentrated in vacuo to leave the product as a colourless oil (6.91 g, 81% yield); 1H NMR (400.0 MHz, DMSO) d 1.39 (9H, s), 3.01 (1H, m), 3.51 (1H, m), 3.71-3.85 (6H, m), 4.29 (1H, m), 5.04 (1H, s), 7.48 (2H, m) and 7.97 (2H, m) ppm.

Workup

  1. customCarbon monoxide gas was bubbled through a reaction mixture
  2. temperaturecooled in an ice bath for 10 mins
  3. customThe reaction vessel was quickly sealed
  4. temperatureThe reaction mixture cooled to rt
  5. filtrationfiltered through celite
  6. washwashing through with methanol
  7. concentrationThe filtrate was concentrated in vacuo and crude product
  8. custompurified by ISCO companion (330 g SiO2 0 to 20% EtOAc/petroleum ether)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9522376ee7f448acb001d7706b22db1b
Source dataset
uspto-grants-2014_07
Patent number
US08765751B2

Reaction notes

Loading…