tert-Butyl 3-(aminomethyl)pyrrolidine-1-carboxylate → HCID 67225102, compound

HRID 1627089Notes

Reaction equation

HRID 1627089 reaction equation
[CH:1]([C:3]1[C:11]2[C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=[N:7][C:6]=2[N:5]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:4]=1)=O.[NH2:23][CH2:24][CH:25]1[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26]1.C([BH3-])#N.[Na+]>CO.CC(O)=O>[C:33]([O:32][C:30]([N:27]1[CH2:28][CH2:29][CH:25]([CH2:24][NH:23][CH2:1][C:3]2[C:11]3[C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=[N:7][C:6]=3[N:5]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:4]=2)[CH2:26]1)=[O:31])([CH3:36])([CH3:35])[CH3:34]

Participants

6

Reactant 3

HCID 2756485tert-Butyl 3-(aminomethyl)pyrrolidine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 58293521HCID 58293521, compound

Product 1

HCID 67225102HCID 67225102, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-tert-butyl 4-methyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate (91 mg, 0.3 mmol) in MeOH (2 mL) was added AcOH (5 drops) and tert-butyl 3-(aminomethyl)pyrrolidine-1-carboxylate (90 mg, 0.45 mmol). After stirring for 60 min at rt, the reaction mixture was cooled to 0° C. Sodium cyanoborohydride (57 mg, 0.9 mmol) was added, and the reaction mixture was stirred for an additional 3 h at rt. The mixture was quenched with water and extracted with ethyl acetate. The combined organic layers washed with saturated NaHCO3 and with brine, dried over Na2SO4, and concentrated in vacuo to give 125 mg of crude 1-tert-butyl 4-methyl 3-(((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate as a colorless oil which was used without further purification. [M+H] found 489.40.

Workup

  1. temperaturethe reaction mixture was cooled to 0° C
  2. stirringthe reaction mixture was stirred for an additional 3 h at rt
  3. customThe mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers washed with saturated NaHCO3 and with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-47624b904d794a6cb1e96a8100e78b0e
Source dataset
uspto-grants-2014_07
Patent number
US08785429B2

Reaction notes

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