Ethyl formate → HCID 54134909, compound

HRID 2180017Notes

Reaction equation

HRID 2180017 reaction equation
[CH:1](OCC)=[O:2].[NH2:6][CH:7]([C:24]1[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=1)[CH2:8][N:9]1[CH2:16][CH:15]2[CH2:17][CH:11]([CH2:12][N:13]([C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[CH2:14]2)[CH2:10]1>>[C:30]([C:27]1[CH:28]=[CH:29][C:24]([CH:7]([NH:6][CH:1]=[O:2])[CH2:8][N:9]2[CH2:10][CH:11]3[CH2:17][CH:15]([CH2:14][N:13]([C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[CH2:12]3)[CH2:16]2)=[CH:25][CH:26]=1)#[N:31]

Participants

3

Reactant 2

HCID 8025Ethyl formateHCID 9885062HCID 9885062, compound

Product 1

HCID 54134909HCID 54134909, compoundYield 40%

Procedure

Ethyl formate (0.5 mL) was added to a stirred solution of iso-propyl 7-[2-amino-2-(4-cyanophenyl)ethyl]-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (from Example 9(viii) above; 0.71 g; 2.0 mmol), and the reaction mixture was refluxed for 5 h. The solvent was evaporated and the residue partitioned between diethyl ether and NaOH (2 M). The organic layer was separated, washed with water, dried and then concentrated. The resulting residue was then recrystallized from MeOH and di-iso-propyl ether to give the title compound in 40% yield.

Workup

  1. temperaturethe reaction mixture was refluxed for 5 h
  2. customThe solvent was evaporated
  3. customthe residue partitioned between diethyl ether and NaOH (2 M)
  4. customThe organic layer was separated
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe resulting residue was then recrystallized from MeOH and di-iso-propyl ether

Sources & evidence

ORD record
ord-dda15fdd30704a148975aff3a87b30fb
Source dataset
uspto-grants-2005_05
Patent number
US06887881B1

Reaction notes

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