Ethyl chloroformate → HCID 68153433, compound

HRID 1405357Notes

Reaction equation

HRID 1405357 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[N:7]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:12][CH2:11][C:10]2([NH:17][CH2:16][CH2:15][N:14]3[CH:18]=[CH:19][CH:20]=[C:13]23)[CH2:9][CH2:8]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:10]12([CH2:11][CH2:12][N:7]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:8][CH2:9]1)[N:17]([C:2]([O:4][CH2:5][CH3:6])=[O:3])[CH2:16][CH2:15][N:14]1[CH:18]=[CH:19][CH:20]=[C:13]21

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 681537801392466-65-7

Product 1

HCID 68153433HCID 68153433, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl chloroformate (328.2 μL, 3.43 mmol) was added to a solution of tert-butyl spiro[3,4-dihydro-2H-pyrrolo[1,2-a]pyrazine-1,4′-piperidine]-1′-carboxylate (500 mg, 1.72 mmol) and K2CO3 (474.3 mg, 3.43 mmol) in acetonitrile (5.0 mL) and the reaction was stirred at room temperature overnight. The reaction was filtered using acetonitrile and the solvent was evaporated under reduced pressure. The compound was dissolved in ethyl acetate and washed with 1N hydrochloric acid and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield 1-tert-butyl 2′-ethyl 3′,4′-dihydro-2′H-spiro[piperidine-4,1′-pyrrolo[1,2-a]pyrazine]-1,2′-dicarboxylate (395 mg, 63%) as an amber oil that was used in the next step without further purification. ESI-MS m/z calc. 363.2, found 364.3 (M+1)+; Retention time: 1.78 minutes (3 minute run).

Workup

  1. filtrationThe reaction was filtered
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe compound was dissolved in ethyl acetate
  4. washwashed with 1N hydrochloric acid and brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-99224d72cf8e4f6b9d1165a198e9bbea
Source dataset
uspto-grants-2014_12
Patent number
US08916565B2

Reaction notes

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