Triethylamine → Phenylmethyl 1-cyano-7-azabicyclo[2.2.1]heptane-7-carboxylate

HRID 2373520Notes

Reaction equation

HRID 2373520 reaction equation
[NH2:1][C:2]([C:4]12[N:10]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH:7]([CH2:8][CH2:9]1)[CH2:6][CH2:5]2)=O.CCN(CC)CC.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[C:2]([C:4]12[N:10]([C:11]([O:13][CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[O:12])[CH:7]([CH2:8][CH2:9]1)[CH2:6][CH2:5]2)#[N:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 21112383HCID 21112383, compound

Product 1

HCID 21112384Phenylmethyl 1-cyano-7-azabicyclo[2.2.1]heptane-7-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Benzyl 1-(aminocarbonyl)-7-azabicyclo[2.2.1]heptane-7-carboxylate (C-36) in dichloromethane was treated at 0° C. with Et3N (2.1 eq.) and trifluoroacetic anhydride (1.1 eq.) was added dropwise. The reaction mixture was stirred at 0° C. for 30 minutes. Then, it was diluted with dichloromethane, washed with saturated NaHCO3 solution, H2O, brine and dried over Na2SO4. Filtration and evaporation afforded the titled compound (C-37).

Workup

  1. additionwas added dropwise
  2. washwashed with saturated NaHCO3 solution, H2O, brine
  3. dry with materialdried over Na2SO4
  4. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-16c327d279d74786a668576c1ffedb8a
Source dataset
uspto-grants-2008_12
Patent number
US07459452B2

Reaction notes

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