Hydrazine hydrate (1:1) → 1-Piperidinecarboxylic acid, 4-[2-(aminooxy)ethoxy]-, 1,1-dimethylethyl ester

HRID 330934Notes

Reaction equation

HRID 330934 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][CH2:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1.O.NN>C(O)C.C(Cl)Cl>[NH2:3][O:12][CH2:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86693960tert-Butyl 4-{2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]ethoxy}piperidine-1-carboxylate

Product 1

HCID 866939611-Piperidinecarboxylic acid, 4-[2-(aminooxy)ethoxy]-, 1,1-dimethylethyl esterYield 86%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-{2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]ethoxy}piperidine-1-carboxylate 70 (0.57 g, 1.46 mmol) in a mixture of ethanol (1 mL) and DCM (6 mL) was added hydrazine hydrate (0.086 g, 1.46 mmol). The reaction mixture was stirred at room temperature for 16 h. Precipitate was filtered off. The filtrate was evaporated and the residue was subjected to chromatography to give 71 (0.327 g, 86%) as a colorless oil.

Workup

  1. filtrationPrecipitate was filtered off
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-b64d595b49d247369e7dc9a3007c2c2b
Source dataset
uspto-grants-2014_11
Patent number
US08877743B2

Reaction notes

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