Triethylamine → HCID 72444859, compound

HRID 1767123Notes

Reaction equation

HRID 1767123 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-e6bfe532e0324573952020e64f9ed5dc
Source dataset
uspto-grants-2007_06
Patent number
US07232819B2

Reaction notes

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