(S)-2-(6-Methoxy-5-nitro-pyridin-2-yloxymethyl)-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester → (S)-2-(5-Amino-6-methoxy-pyridin-2-yloxymethyl)-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester

HRID 390306Notes

Reaction equation

HRID 390306 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[C:17]([O:24][CH3:25])[N:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[C:17]([O:24][CH3:25])[N:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 66883424(S)-2-(6-Methoxy-5-nitro-pyridin-2-yloxymethyl)-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester

Product 1

HCID 66883332(S)-2-(5-Amino-6-methoxy-pyridin-2-yloxymethyl)-pyrrolidine-1-carboxylic Acid Tert-Butyl EsterYield 96.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (S)-2-(6-methoxy-5-nitro-pyridin-2-yloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.11 g, 0.32 mmol) in methanol (11 ml) was hydrogenated using the ThalesNano H-Cube® hydrogenation reactor employing a 10% palladium on charcoal catalyst cartridge. After concentration of the solution under reduced pressure 0.10 g (92.6%) of the title compound were obtained.

Sources & evidence

ORD record
ord-e397307cfb0c47918e493be35fc99d26
Source dataset
uspto-grants-2013_02
Patent number
US08383641B2

Reaction notes

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