Hydrochloric Acid → HCID 66705287, compound

HRID 424963Notes

Reaction equation

HRID 424963 reaction equation
C([Li])(CC)C.[C:6]([O:10][C:11]([N:13]1[CH2:17][CH:16]2[CH2:18][CH2:19][CH2:20][CH:15]2[CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].CN(C)CCN(C)C.[CH2:29]([O:31][C:32](Cl)=[O:33])[CH3:30].Cl.O1CCCC1>C1CCCCC1.C(OCC)C.C(OCC)(=O)C>[CH:14]1([C:32]([O:31][CH2:29][CH3:30])=[O:33])[CH:15]2[CH2:20][CH2:19][CH2:18][CH:16]2[CH2:17][N:13]1[C:11]([O:10][C:6]([CH3:9])([CH3:7])[CH3:8])=[O:12]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 10928Ethyl chloroformateHCID 60041335HCID 60041335, compoundHCID 178418400CID 53628100

Product 1

HCID 66705287HCID 66705287, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

Sec-butyl lithium (26.8 mL of a 1.4M solution in cyclohexane; 1.2 eq) was added dropwise to a solution of N-tert-butyloxycarbonyl-octahydrocyclopenta[c]pyrrole (6.6 gm) and tetramethylethylenediamine (TMEDA) (4.69 mL, 1 eq) in diethyl ether (63 mL) at −78° C., and allowed to stir for 1.5 hours. Ethylchloroformate (6 mL, 2 eq) in diethylether (10 mL) was added dropwise to the reaction mixture (maintaining the temperature at −78° C.), and the reaction mixture was allowed to rise to room temperature over a period of 2.5 hours. The temperature was then reduced to −78° C., and quenched by careful addition of hydrochloric acid in tetrahydrofuran (2.2 eq). The reaction was then diluted with ethyl acetate, and washed successively with 1N hydrochloric acid, water, brine, and then dried over anhydrous sodium sulfate. Evaporation of the organic layer under reduced pressure gave crude product, which was purified by column chromatography on silica gel, eluting with 9% ethyl acetate/hexane, to give 2-tert-butyl 1-ethyl hexahydrocyclopenta[c]pyrrole-1,2(1H)-dicarboxylate (2.5 gm).

Workup

  1. waitto rise to room temperature over a period of 2.5 hours
  2. customwas then reduced to −78° C.
  3. washwashed successively with 1N hydrochloric acid, water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customEvaporation of the organic layer under reduced pressure
  6. customgave crude product, which
  7. customwas purified by column chromatography on silica gel
  8. washeluting with 9% ethyl acetate/hexane

Sources & evidence

ORD record
ord-4ce25ec026db40c685b380e9848f11c9
Source dataset
uspto-grants-2012_01
Patent number
US08106059B2

Reaction notes

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