Hydrazine hydrate (1:1) → (RS)-2-Hydrazinocarbonylmethyl-piperidine-1-carboxylic acid tert butyl ester

HRID 549326Notes

Reaction equation

HRID 549326 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][C:15]([O:17]C)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[NH2:20][NH2:21]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][C:15]([NH:20][NH2:21])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 11572435Methyl N-boc-2-piperidineacetate

Product 1

HCID 59789366(RS)-2-Hydrazinocarbonylmethyl-piperidine-1-carboxylic acid tert butyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Methoxycarbonylmethyl-piperidine-1-carboxylic acid tert butyl ester (8.14 g) in ethanol (150 ml) was treated with hydrazine hydrate (19 ml) and the mixture boiled for 16 h. Solvent was removed at reduced pressure and the residue azeotroped with toluene to give the title compound (8.34 g)

Workup

  1. customSolvent was removed at reduced pressure
  2. customthe residue azeotroped with toluene

Sources & evidence

ORD record
ord-431f2394dca545c0abb3554f771d0e1c
Source dataset
uspto-grants-2011_05
Patent number
US07943645B2

Reaction notes

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