4-Fluoroaniline → HCID 66582141, compound

HRID 73641Notes

Reaction equation

HRID 73641 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C[Al](C)C.[O:13]1[C@@H:23]2[C@:14]31[C@@H:19]([CH2:20][CH2:21][CH2:22]2)[O:18][CH2:17][CH2:16][CH2:15]3.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C(Cl)Cl.O>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C@@H:23]2[CH2:22][CH2:21][CH2:20][C@@H:19]3[C@:14]2([OH:13])[CH2:15][CH2:16][CH2:17][O:18]3)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 97314-FluoroanilineHCID 9855836Potassium sodium tartarateHCID 16682925TrimethylaluminumHCID 86668662HCID 86668662, compound

Product 1

HCID 66582141HCID 66582141, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolved 55 uL 4-fluoroaniline in 1.3 mL CH2Cl2 then cooled to 0° C. and added 0.21 mL AlMe3 (2.0M in toluene). Warmed to RT, stirred for 30 minutes, then added 50 mg (1aS,4aR,8aS)-hexahydro-1aH,6H-oxireno[e]chromene (7-5) in 1.0 mL CH2Cl2. Stirred for two hours at RT, then sat. sodium potassium tartrate solution was added dropwise to the reaction, allowing gas evolution to cease between drops, until no further gas evolution was noted. The mixture was diluted with water, then extracted with CH2Cl2. The extract was dried over Na2SO4, filtered, concentrated, then purified on silica (0-40% EtOAc in hexanes) to yield the title compound. 1H NMR (500 MHz, CDCl3) δ=1.42-1.69 (m, 7H), 1.90-2.09 (m, 3H), 2.47 (s, 1H), 3.38-3.48 (m, 3H), 3.53 (s, broad, 1H), 3.92-3.95 (m, 1H), 6.54-6.59 (m, 2H), 6.84-7.26 (m, 2H) ppm. HRMS (ES) m/z M±H calc'd: 266.1551. found 266.1551.

Workup

  1. temperatureWarmed to RT
  2. stirringStirred for two hours at RT
  3. extractionextracted with CH2Cl2
  4. dry with materialThe extract was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified on silica (0-40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-56369c6cbce64a48b452e9793acf978a
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Reaction notes

Loading…