Sodium Carbonate → HCID 22859462, compound

HRID 265000Notes

Reaction equation

HRID 265000 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].[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+].[C:34]1(B(O)O)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[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:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:10][CH2:9]1)[CH2:5][CH2:6][CH3:7])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 433294Lithium ChlorideHCID 10619825(R)-3-(N-Isopropyl,N-n-propylamino)-5-trifluoromethanesulfonyloxychroman

Product 1

HCID 22859462HCID 22859462, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

(R)-3-(N-Isopropyl,N-n-propylamino)-5-trifluoromethanesulfonyloxychroman (1 g, 2.6 mmol) was dissolved in toluene (25 mL) under a nitrogen atmosphere. Ethanol (11.5 mL), LiCl (0.22 g, 5.2 mmol), Na2CO3 (2M, 3.8 mL), Pd(PPh3)4 (0.054 g, 0.047 mmol) and phenylboronic acid (0.38 g, 3.1 mmol) were added and the reaction mixture was stirred at 90° C. for 7 h. The solvent removed in vacuo until 15 mL was left. The residue was diluted with diethyl ether, washed with NH3 (2M) twice and dried (MgSO4). Removal of the solvent in vacuo gave a yellow-brownish oily residue which was purified by flash chromatography )SiO2, CH2Cl2) to give the title compound in 86% yield (0.7 g). α=-50.7° (MeOH, 0.1M, 22° C.). The HCl-salt was precipitated from ether by the slow addition of HCl in ether to an ice-cold solution of the base. The crude salt was recrystallized from EtOAc/diethyl ether to give 650 mg of needle-like crystals. Mp. 141°-142° C.

Workup

  1. customThe solvent removed in vacuo until 15 mL
  2. waitwas left
  3. additionThe residue was diluted with diethyl ether
  4. washwashed with NH3 (2M) twice
  5. dry with materialdried (MgSO4)
  6. customRemoval of the solvent in vacuo
  7. customgave a yellow-brownish oily residue which
  8. customwas purified by flash chromatography )SiO2, CH2Cl2)

Sources & evidence

ORD record
ord-d476e0084f7b4d12b9b129f035f1c574
Source dataset
uspto-grants-1997_07
Patent number
US05646309

Reaction notes

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