Triethylamine → HCID 10108338, compound

HRID 37682Notes

Reaction equation

HRID 37682 reaction equation
[CH:1]([N:4]([C@@H:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2OS(C(F)(F)F)(=O)=O)[O:10][CH2:9]1)[CH2:5][CH2:6][CH3:7])([CH3:3])[CH3:2].C(N(CC)CC)C.CN([CH:36]=[O:37])C.[CH3:38][OH:39]>>[CH:1]([N:4]([C@@H:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[C:38]([O:37][CH3:36])=[O:39])[O:10][CH2:9]1)[CH2:5][CH2:6][CH3:7])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 10619825(R)-3-(N-Isopropyl,N-n-propylamino)-5-trifluoromethanesulfonyloxychromanHCID 21901440N,N-dimethylformamide methanol

Product 1

HCID 10108338HCID 10108338, compoundYield 82%

Conditions

Temperature
70 °C

Procedure

(R)-3-(N-Isopropyl,N-n-propylamino)-5-trifluoromethanesulfonyloxychroman (4.0 g, 10.5 mmol), triethylamine (2.3 g, 23.1 mmol) and a mixture of DMF/MeOH (18 mL, 6:2) was mixed in a three necked round-bottom flask. The flask was evacuated followed by inlet of CO-gas (repeated two times). Finally 1,3-bis(diphenylphosphino)propane (0.11 g) and palladium(II)acetate (0.07 g) was added. The mixture was stirred at 70° C. for 17 hours. The reaction mixture was diluted with diethyl ether, washed with 2M NH3 and dried (MgSO4). Removal of solvent in vacuo gave a brown oily residue which was purified by flash chromatography (SiO2, CH2Cl2 /EtOAc; 10:1) to give the title compound in 82% yield (2.5 g). [α]D21 =-131.6° (MeOH, 0.1M) GC-MS(70 eV)=291 (M+), 262 (100%)

Workup

  1. additionwas mixed in a three necked round-bottom flask
  2. customThe flask was evacuated
  3. customfollowed by inlet of CO-gas (repeated two times)
  4. additionFinally 1,3-bis(diphenylphosphino)propane (0.11 g) and palladium(II)acetate (0.07 g) was added
  5. additionThe reaction mixture was diluted with diethyl ether
  6. washwashed with 2M NH3
  7. dry with materialdried (MgSO4)
  8. customRemoval of solvent in vacuo
  9. customgave a brown oily residue which
  10. customwas purified by flash chromatography (SiO2, CH2Cl2 /EtOAc; 10:1)

Sources & evidence

ORD record
ord-bf43e59ec7dc43a787b9111141b92833
Source dataset
uspto-grants-1995_05
Patent number
US05420151

Reaction notes

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