Aniline → HCID 86649084, compound

HRID 1099014Notes

Reaction equation

HRID 1099014 reaction equation
[C:1]1([CH:7]2[N:12]3[CH:8]2[CH:9](O)O[CH:11]3[CH:13]2[CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:14]2)[CH:6]=[CH:5]C=CC=1.NC1C=CC=CC=1.[BH3-]C#N.[Na+].C([O-])(O)=O.[Na+]>CO.O.C(O)(=O)C>[C:7]1([NH:12][CH2:11][C@H:13]2[C@H:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:14]2)[CH:1]=[CH:6][CH:5]=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 6115AnilineHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 250017156-Phenyl-2-(3-phenylaziridin-2-yl)-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol

Product 1

HCID 86649084HCID 86649084, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In a flamed-dried round bottom flask equipped with a rubber septum in order to maintain a nitrogen atmosphere was added 2a (58.8 mg, 0.2 mmol) and aniline (43.7 μl, 0.48 mmol) dissolved in 5 ml of anhydrous MeOH. The reaction was stirred for 10 minutes, then NaCNBH3 (40.2 mg, 0.64 mmol) was added. The reaction was allowed to stir for 5 hours while maintaining pH 7 through addition of acetic acid when required. NaHCO3 was then carefully added to the reaction mixture and stirred for 5 minutes. Water was added and the aqueous mixture was extracted 3 times with Et2O. The collected organic phases were washed with water, then brine, and dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified using flash column chromatography (silica gel; 5% MeOH in CH2Cl2) to afford the title compound as a white solid in 99% yield. Mp=96-97° C. 1H NMR (200 MHz. CDCl3) δ:7.40-7.10 (m, 7H), 6.78-6.62 (m, 3H), 3.51 (dd, J=13.6 Hz, 4.2 Hz, 1H), 3.4 (very bs, 2H), 3.28 (dd, J=13.6 Hz, 7.5 Hz, 1H), 2.86 (d, J=2.8 Hz, 1H), 2.50-2.35 (m, 1H) ppm. 13C NMR (50 MHz. CDCl3) δ: 148.3, 139.7, 129.5, 129.4, 128.8, 127.4, 125.8, 118.1, 115.3, 113.2, 46.4, 40.3, 38.0 ppm. Rf=0.14 (7:3 hexanes/EtOAc).

Workup

  1. customIn a flamed-dried round bottom flask equipped with a rubber septum in order
  2. temperatureto maintain a nitrogen atmosphere
  3. stirringto stir for 5 hours
  4. temperaturewhile maintaining pH 7
  5. stirringstirred for 5 minutes
  6. extractionthe aqueous mixture was extracted 3 times with Et2O
  7. washThe collected organic phases were washed with water
  8. dry with materialbrine, and dried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was purified

Sources & evidence

ORD record
ord-1f22ec6e03f7438d8d2c7fffab164c41
Source dataset
uspto-grants-2012_03
Patent number
US08143375B2

Reaction notes

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