Trifluoroacetic acid → 7-Benzyl-1-cyano-2-oxa-7-azabicyclo[3.3.0]octane

HRID 1900228Notes

Reaction equation

HRID 1900228 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]=[C:2]1[C:6]#[N:7].C(N(CC)CC)C.FC(F)(F)C(O)=O.[CH2:22]([N:29]([CH2:35]OC)[CH2:30][Si](C)(C)C)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH2:22]([N:29]1[CH2:30][C:2]2([C:6]#[N:7])[CH:3]([CH2:4][CH2:5][O:1]2)[CH2:35]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 136240424,5-Dihydrofuran-2-carbonitrile

Product 1

HCID 217047477-Benzyl-1-cyano-2-oxa-7-azabicyclo[3.3.0]octane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

14.4 g (0.15 mol) of 4,5-dihydrofuran-2-carbonitrile are introduced in 300 ml of absolute methylene chloride, 1.8 g of triethylamine and 1.8 g of trifluoroacetic acid are added, and the mixture is warmed to 40° C. 42.6 g (0.15 mol) of N-benzyl-N-methoxymethyl-N-trimethylsilylmethylamine are added dropwise to this mixture which is then stirred at 40° C. for 15 hours. It is then washed with 50 ml of saturated sodium hydrogen carbonate solution, dried over MgSO4, concentrated and distilled twice.

Workup

  1. washIt is then washed with 50 ml of saturated sodium hydrogen carbonate solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. distillationdistilled twice

Sources & evidence

ORD record
ord-ee1860aab4bf4ac7beec01d2054018d8
Source dataset
uspto-grants-1996_11
Patent number
US05574161

Reaction notes

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