HCID 66757999, compound → HCID 66758019, compound

HRID 557018Notes

Reaction equation

HRID 557018 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([N:13]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[N+:27]([O-])=O)[CH2:14][C:15]([O:17]C)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([N:13]2[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[NH:27][C:15](=[O:17])[CH2:14]2)[CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 66757999HCID 66757999, compound

Product 1

HCID 66758019HCID 66758019, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[(4-Chloro-2-nitro-benzyl)-methoxycarbonylmethyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester (1.04 g, 2.4 mmol) in ethyl acetate (20 mL) was added 10% Pd/C. Hydrogenolysis of the reaction solution at rt under atmospheric pressure provided the desired product after 1.5 h. The reaction mixture was filtered through a pad of celite and concentrated. The crude product (662 mg, 1.7 mmol) was dissolved in DMF (5 mL) and to it was added 60% NaH (100 mg, 2.5 mmol). The resultant solution was stirred at rt overnight. The reaction was quenched with water and extracted with ethyl ether. The organic extract was dried over MgSO4, filtered and concentrated to get the crude product. Purification on SiO2 provided the desired product. LCMS (retention time=1.89, ES+; 310)

Sources & evidence

ORD record
ord-fad0cb5346754e0e97591d1e9efa904a
Source dataset
uspto-grants-2011_11
Patent number
US08058287B2

Reaction notes

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