Dichloromethane methanol → 1-((1R,3S)-3-aminocyclohexyl)pyrrolidin-2-one

HRID 74973Notes

Reaction equation

HRID 74973 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C@@H:7]1[CH2:12][CH2:11][CH2:10][C@H:9]([NH:13]C(=O)OCC2C=CC=CC=2)[CH2:8]1.CO.C(Cl)Cl>CO.[Pd]>[NH2:13][C@H:9]1[CH2:10][CH2:11][CH2:12][C@@H:7]([N:3]2[CH2:4][CH2:5][CH2:6][C:2]2=[O:1])[CH2:8]1

Participants

5

Reactant 2

HCID 21226129Dichloromethane methanolHCID 68101804benzyl (1S,3R)-3-(2-oxopyrrolidin-1-yl)cyclohexylcarbamate2×

Product 1

HCID 281688041-((1R,3S)-3-aminocyclohexyl)pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A degassed solution of benzyl (1S,3R)-3-(2-oxopyrrolidin-1-yl)cyclohexylcarbamate, 45b, (0.165 g, 0.522 mmol) and Pd on C (10% wet, Degussa, 0.050 g, 0.024 mmol) in MeOH (15 mL) was placed under H2 atm (balloon). After 105 min, TLC (10% MeOH-DCM) indicated complete consumption of starting material. H2 was removed and the solution filtered and concentrated in vacuo. The crude product was azeotroped with CH3CN (2×) to remove any residual MeOH and provided the desired product (96 mg): FIA (M+H+) 183.27

Workup

  1. customconsumption of starting material
  2. customH2 was removed
  3. filtrationthe solution filtered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was azeotroped with CH3CN (2×)
  6. customto remove any residual MeOH

Sources & evidence

ORD record
ord-fbb4b02b32ed41f180ce1d34284ea0a0
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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