Sodium bis(trimethylsilyl)amide → 3-Benzyl-3-azabicyclo[3.1.0]hexane-1-carbonitrile

HRID 373690Notes

Reaction equation

HRID 373690 reaction equation
[CH2:1]([N:8]([CH2:13][CH:14](S(C)(=O)=O)[CH2:15]S(C)(=O)=O)[CH2:9][CH2:10][C:11]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>C1C=CC=CC=1.O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH:14]2[C:10]([C:11]#[N:12])([CH2:15]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 20089986HCID 20089986, compound

Product 1

HCID 121996873-Benzyl-3-azabicyclo[3.1.0]hexane-1-carbonitrileYield 49%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-Benzyl-N-(2-cyanoethyl)-2,3-dimethanesulfonylpropylamine (32.25 g, 85.2 mmol) was dissolved in benzene (800 ml), cooled to -10°, and treated with sodium hexamethyldisilazide (170 ml of a 1M solution in tetrahydrofuran, 170 mmol). After 2 hours, the reaction mixture was quenched with saturated ammonium chloride solution, and the mixture was extracted three times with methylene chloride. The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatographic purification (eluant: 4:1 hexane:ethyl acetate) gave the title product as a yellow oil (8.23 g, 41.5 mmol, 49% yield). 1H NMR (CDCl ): 7.26 (m, 5H), 3.59 (s, 2H), 3.11 (d, J=9 Hz, 1H), 2.94 (d, J=9 Hz, 1H), 2.54 (d, J=9 Hz, 1H), 2.47 (dd, J=10, 4 Hz, 1H), 2.03 (m, 1H), 1.57 (m, 1H), 1.10 (dd, J=8, 5 Hz, 1H).

Workup

  1. temperaturecooled to -10°
  2. customthe reaction mixture was quenched with saturated ammonium chloride solution
  3. extractionthe mixture was extracted three times with methylene chloride
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customChromatographic purification (eluant: 4:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-842539d109bd452390c1f646e55b6f93
Source dataset
uspto-grants-1992_11
Patent number
US05164402

Reaction notes

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