Dichloromethane → Hexahydrocyclopenta(c)pyrrol-5(1H)-one

HRID 1925077Notes

Reaction equation

HRID 1925077 reaction equation
C(OC(=O)NCC([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1C#N)=O)(C)(C)C.F[C:20](F)(F)[C:21]([OH:23])=O.Cl[CH2:27]Cl>>[CH2:15]1[CH:14]2[CH2:27][C:21](=[O:23])[CH2:20][CH:13]2[CH2:12][NH:11]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 67519316(S)-tert-butyl 2-(2-cyanopyrrolidin-1-yl)-2-oxoethylcarbamate

Product 1

HCID 46911901Hexahydrocyclopenta(c)pyrrol-5(1H)-one

Conditions

Temperature
0 °C

Procedure

5-oxo-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester 1e (0.32 g, 1.42 mmol) was dissolved in 10 mL of dichloromethane, and trifluoroacetic acid (3.27 mL, 42.7 mmol) was then added to the solution in an ice-water bath. Upon completion of the addition, the reaction mixture was stirred at 0° C. for 30 minutes, then the solvent was evaporated to dryness to obtain the title compound hexahydro-cyclopenta[c]pyrrol-5-one triflutate 1f which was directly used in the further reaction.

Workup

  1. additionUpon completion of the addition
  2. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-6d0293a7ed654f18b8e1d0662a34f259
Source dataset
uspto-grants-2012_05
Patent number
US08178575B2

Reaction notes

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