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

HRID 275196Notes

Reaction equation

HRID 275196 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 (CDCl3): 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-c85c657fb5e148a6a2810e39a5278a69
Source dataset
uspto-grants-1995_02
Patent number
US05391763

Reaction notes

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