Hydrazine hydrate (1:1) → tert-Butyl 4-aminomethyl-4-fluoropiperidine-1-carboxylate

HRID 2112549Notes

Reaction equation

HRID 2112549 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][N:16]2C(=O)C3C(=CC=CC=3)C2=O)([F:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.NN>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([CH2:15][NH2:16])([F:14])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 53415317Tert-butyl 4-((1,3-dioxoisoindolin-2-yl)methyl)-4-fluoropiperidine-1-carboxylate

Product 1

HCID 40152119tert-Butyl 4-aminomethyl-4-fluoropiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The 4-[(1,3-dioxoisoindolin-2-yl)methyl]-4-fluoropiperidinecarboxylic acid tert-butyl ester was dissolved in ethanol (200 mL), and then hydrazine monohydrate (10.0 mL) was added. After stirring at room temperature for 2 hours, the precipitated solid was filtered out and the filtrate was concentrated under reduced pressure. The obtained crudely purified product was further purified by silica gel column chromatography (5% MeOH/CH2Cl2) to obtain 4-(aminomethyl)-4-fluoropiperidinecarboxylic acid tert-butyl ester. The compound was identified by 1H-NMR. The yield was 3.23 g (76%).

Workup

  1. filtrationthe precipitated solid was filtered out
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained crudely purified product
  4. customwas further purified by silica gel column chromatography (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-3358ccc25ea64954a6cb22a8b49b684f
Source dataset
uspto-grants-2009_04
Patent number
US07524841B2

Reaction notes

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