Ethyl Acetate → 4-[5-Amino-4-(2-hydroxymethyl-pyrrolidine-1-carbonyl)-2-methoxy-phenoxy]-butyric acid methyl ester

HRID 476398Notes

Reaction equation

HRID 476398 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[C:12]([N+:14]([O-])=O)[C:11]([C:17]([N:19]2[CH2:23][CH2:22][CH2:21][CH:20]2[CH2:24][OH:25])=[O:18])=[CH:10][C:9]=1[O:26][CH3:27].[H][H].CCOC(C)=O>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[C:12]([NH2:14])[C:11]([C:17]([N:19]2[CH2:23][CH2:22][CH2:21][CH:20]2[CH2:24][OH:25])=[O:18])=[CH:10][C:9]=1[O:26][CH3:27]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 68844115HCID 68844115, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 688432654-[5-Amino-4-(2-hydroxymethyl-pyrrolidine-1-carbonyl)-2-methoxy-phenoxy]-butyric acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

The nitro ester 14 (38.4 g, 97 mmol) was dissolved in ethanol (2 batches of 19.2 g in 200 mL ethanol per 500 mL hydrogenation flask). 10% Pd/C was added as a slurry in ethanol (1 g per batch) and the mixture was hydrogenated in a Parr hydrogenation apparatus at 40 psi until no further hydrogen uptake was observed. Reaction completion was confirmed by TLC analysis (EtOAc) and the mixture was filtered through celite. The solvent was removed in vacuo and the amine 15 was used directly in the next step. (35.4 g, quantitative yield).

Workup

  1. customReaction completion
  2. filtrationthe mixture was filtered through celite
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-26bc706d10534f7eab5904a667e9170b
Source dataset
uspto-grants-2014_01
Patent number
US08637664B2

Reaction notes

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