Triethylamine → HCID 72444859, compound

HRID 2373521Notes

Reaction equation

HRID 2373521 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][OH:10].[C:11]([C:13]12[N:19]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH:16]([CH2:17][CH2:18]1)[CH2:15][CH2:14]2)#[N:12].[CH3:30][O:31][C:32]([C:34]#[C:35][C:36]([O:38][CH3:39])=[O:37])=[O:33]>CO>[CH3:30][O:31][C:32](=[O:33])[C:34]([O:10][N:9]=[C:11]([NH2:12])[C:13]12[N:19]([C:20]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:21])[CH:16]([CH2:17][CH2:18]1)[CH2:15][CH2:14]2)=[CH:35][C:36]([O:38][CH3:39])=[O:37]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 12980Dimethyl acetylenedicarboxylateHCID 443297Hydroxyamine hydrochlorideHCID 21112384Phenylmethyl 1-cyano-7-azabicyclo[2.2.1]heptane-7-carboxylate

Product 1

HCID 72444859HCID 72444859, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Triethyl amine (1.5 eq.), hydroxylamine hydrochloride (1.3 eq.) were added to a solution of benzyl 1-cyano-7-azabicyclo[2.2.1]heptane-7-carboxylate (C-37) in absolute methanol. The mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, the residue was dissolved in chloroform and treated with dimethylacetylene dicarboxylate (2 eq.) for 14 hours at 60° C. The reaction mixture was then concentrated and the resulting crude oil was purified by flash chromatography (petroleum ether/EtOAc 1:1) to give the titled compound (C-38) as a mixture of isomers.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in chloroform
  3. concentrationThe reaction mixture was then concentrated
  4. customthe resulting crude oil was purified by flash chromatography (petroleum ether/EtOAc 1:1)

Sources & evidence

ORD record
ord-8c1ebf4a366c41d8ae5a193a5d2d36d8
Source dataset
uspto-grants-2008_12
Patent number
US07459452B2

Reaction notes

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