(S)-1-tert-butyl 2-methyl 4-(6-aminopyridin-3-yl)-1H-pyrrole-1,2(2H,5H)-dicarboxylate → 1-(tert-Butyl) 2-methyl (2S,4R)-4-(6-aminopyridin-3-yl)pyrrolidine-1,2-dicarboxylate

HRID 595827Notes

Reaction equation

HRID 595827 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:10]([C:20]([O:22][CH3:23])=[O:21])[CH:9]=2)=[CH:4][CH:3]=1>CO.[Pd]>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[C@H:10]([C:20]([O:22][CH3:23])=[O:21])[CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 118046073(S)-1-tert-butyl 2-methyl 4-(6-aminopyridin-3-yl)-1H-pyrrole-1,2(2H,5H)-dicarboxylate

Product 1

HCID 1180462431-(tert-Butyl) 2-methyl (2S,4R)-4-(6-aminopyridin-3-yl)pyrrolidine-1,2-dicarboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A degassed solution of (S)-1-tert-butyl 2-methyl 4-(6-aminopyridin-3-yl)-1H-pyrrole-1,2(2H,5H)-dicarboxylate (0.955 g, 2.99 mmol) in methanol (30 mL) was treated with 10% Pd/C (0.183 g, 0.172 mmol), then maintained under an atmosphere of hydrogen for 3 h. At completion, the reaction then filtered over a pad of Celite and concentrated to provide (2S,4R)-1-tert-butyl 2-methyl 4-(6-aminopyridin-3-yl)pyrrolidine-1,2-dicarboxylate (0.95 g. 99% yield). LCMS (m/z): 322.5 (MH+), 0.52 min.

Workup

  1. temperaturemaintained under an atmosphere of hydrogen for 3 h
  2. customAt completion, the reaction
  3. filtrationthen filtered over a pad of Celite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f2211cfa9b0a4ca28ceeb0481806966f
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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