Hydrazine → (R)-1-Boc-piperidine-3-carboxylic acid hydrazide

HRID 1465697Notes

Reaction equation

HRID 1465697 reaction equation
[N:1]1([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH2:4][C@@H:3]([C:7](OCC)=[O:8])[CH2:2]1.[NH2:19][NH2:20]>CO>[NH:19]([C:7]([C@@H:3]1[CH2:4][CH2:5][CH2:6][N:1]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:2]1)=[O:8])[NH2:20]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 15144461-tert-Butyl 3-ethyl (3R)-piperidine-1,3-dicarboxylate

Product 1

HCID 29922274(R)-1-Boc-piperidine-3-carboxylic acid hydrazide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Stirred a solution of (R)-1-tert-butyl 3-ethyl piperidine-1,3-dicarboxylate (5 g, 19.4 mmol), hydrazine (anhydrous; 2 ml) in MeOH (5 ml) in a microwave oven at 100° C. for 3 hours. Cooled and solvent was evaporated. Chromatographed residue on silica gel eluting with 3% MeOH: DCM to yield (R)-tert-butyl 3-(hydrazinecarbonyl)piperidine-1-carboxylate as colorless oil (5.1 g).

Workup

  1. temperatureCooled
  2. customsolvent was evaporated

Sources & evidence

ORD record
ord-05a2fb6bb445453a948df20e035ed925
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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