1-tert-Butyl 2-methyl (2S,4R)-4-{[6-(benzyloxy)pyridin-2-yl]oxy}pyrrolidine-1,2-dicarboxylate → HCID 178501329, compound

HRID 1255523Notes

Reaction equation

HRID 1255523 reaction equation
C([O:8][C:9]1[N:14]=[C:13]([O:15][C@H:16]2[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:18]([C:28]([O:30][CH3:31])=[O:29])[CH2:17]2)[CH:12]=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].CCO>[OH:8][C:9]1[N:14]=[C:13]([O:15][C@H:16]2[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[C@H:18]([C:28]([O:30][CH3:31])=[O:29])[CH2:17]2)[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 581580861-tert-Butyl 2-methyl (2S,4R)-4-{[6-(benzyloxy)pyridin-2-yl]oxy}pyrrolidine-1,2-dicarboxylate

Product 1

HCID 178501329HCID 178501329, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A Parr jar was charged with the product of Step 3 (6.50 g, 15.17 mmol), EtOH (100 ml), and 10% Pd/C (0.250 g, 2.349 mmol). Hydrogenated at 48 psi. Reaction complete after 18 hours. Filtered through celite. Evaporation of the filtrate gave the title compound as a white foam. (4.95 g, 14.63 mmol, 96% yield). LCMS (ES+) m/z 339.3 (M+H)+.

Workup

  1. customReaction complete after 18 hours
  2. filtrationFiltered through celite
  3. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-85a6378b91714bd1b5c378dacc337b9c
Source dataset
uspto-grants-2013_06
Patent number
US08461107B2

Reaction notes

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