1-BOC-3-Aminopiperidine → HCID 67224484, compound

HRID 1968189Notes

Reaction equation

HRID 1968189 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(OC(C)(C)C)=O)[CH:4]=1)=O.[NH2:23][CH:24]1[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]1.[B-]C#N.[Na+]>CO.C(O)(=O)C>[C:33]([O:32][C:30]([N:26]1[CH2:27][CH2:28][CH2:29][CH: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[NH:5][CH:4]=2)[CH2:25]1)=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

5

Reactant 3

HCID 5458091-BOC-3-AminopiperidineHCID 20587905Sodium cyanoborohydride [MI]HCID 58293521HCID 58293521, compound

Product 1

HCID 67224484HCID 67224484, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

To a solution of 1-tert-butyl 4-methyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate (304 mg, 1.00 mmol) in 9:1 MeOH-Acetic Acid (2 mL) at 0° C. was added tert-butyl 3-aminopiperidine-1-carboxylate (300 mg, 1.50 mmol) and the reaction mixture was stirred at rt for 1 h. Sodium cyanotrihydroborate (314 mg, 5.00 mmol) was added slowly portion wise and the reaction mixture was stirred at rt over night, quenched with water, and extracted with ethyl acetate. The combined organic layers were washed with saturated NaHCO3 and with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica gel chromatography (30% to 70% Hexane-EtOAc) to give 307 mg of methyl 3-((1-(tert-butoxycarbonyl)piperidin-3-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylate as a colorless oil. [M+H] found 389.

Workup

  1. stirringthe reaction mixture was stirred at rt over night
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with saturated NaHCO3 and with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography (30% to 70% Hexane-EtOAc)

Sources & evidence

ORD record
ord-03f72ac79c09400aaa1775c73b11d2b9
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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