Ethyl Acetate → 4-Amino-1-Boc-piperidine

HRID 369995Notes

Reaction equation

HRID 369995 reaction equation
[N:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)=[N+]=[N-].C(OCC)(=O)C>CO.CCCCCC.[Pd]>[NH2:1][CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]1

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 114587941,1-Dimethylethyl 4-azido-1-piperidinecarboxylate

Product 1

HCID 12682914-Amino-1-Boc-piperidineYield 97.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

A solution of 4.05 g (17.9 mmol) of 4-azido-1-(tert-butoxycarbonyl)piperidine from Step A in 50 mL of methanol was hydrogenated with 350 mg of 10% Pd/C under a hydrogen balloon for 16 h when the reaction was complete by TLC (10% ethyl acetate in hexane). The catalyst was filtered off and the volatiles removed in vacuo to give 3.5 g of title compound which was used directly in subsequent reactions.

Workup

  1. customfor 16 h
  2. filtrationThe catalyst was filtered off
  3. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-c776b7bbe70e4f83af60216280a3d539
Source dataset
uspto-grants-2000_10
Patent number
US06140349

Reaction notes

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