HCID 86708686, compound → HCID 86708687, compound

HRID 921791Notes

Reaction equation

HRID 921791 reaction equation
[Cl:1][C:2]1[C:20]([N+:21]([O-])=O)=[CH:19][C:18]([C:24]#[N:25])=[CH:17][C:3]=1[O:4][CH:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]1>CO.[Pd]>[NH2:21][C:20]1[C:2]([Cl:1])=[C:3]([CH:17]=[C:18]([C:24]#[N:25])[CH:19]=1)[O:4][CH:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]1

Participants

4

Reactant 1

HCID 86708686HCID 86708686, compound

Product 1

HCID 86708687HCID 86708687, compoundYield 18.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (+/−)-tert-butyl 3-(2-chloro-5-cyano-3-nitrophenoxy)pyrrolidine-1-carboxylate (278 mg, 0.756 mmol) and Pd/C (80 mg, 0.038 mmol) in Methanol (20 mL) was hydrogenated at 20 psi for 2 h. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated. The crude product was purified by flash chromatography on silica gel using an automated ISCO system (40 g column, eluting with 5-60% ethyl acetate/hexanes) to give (+/−)-tert-butyl 3-(3-amino-2-chloro-5-cyanophenoxy)pyrrolidine-1-carboxylate (48 mg).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated
  3. customThe crude product was purified by flash chromatography on silica gel using
  4. washan automated ISCO system (40 g column, eluting with 5-60% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-e2d83c665245474e8f116f2f60ad41f5
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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