Hydrazine hydrate (1:1) → Tert-butyl (3s,4r)-4-(aminomethyl)-3-hydroxypiperidine-1-carboxylate

HRID 344295Notes

Reaction equation

HRID 344295 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][N:15]2C(=O)C3C(=CC=CC=3)C2=O)[C@H:10]([OH:26])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.NN>C(O)C>[NH2:15][CH2:14][C@H:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:9][C@H:10]1[OH:26]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 70075564cis-1-tert-butoxycarbonyl-4-(2,3-dihydro-1,3-dioxo-1 H-isoindol-2-yl)methyl-3-hydroxypiperidine

Product 1

HCID 57983247Tert-butyl (3s,4r)-4-(aminomethyl)-3-hydroxypiperidine-1-carboxylateYield 110.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of cis-l-tert-butoxycarbonyl-4-(2,3-dihydro-1,3-dioxo-1 H-isoindol-2-yl)methyl-3-hydroxypiperidine (2.4 g) in ethanol (35 ml) was added hydrazine monohydrate (0.48 ml), and the resulting mixture was stirred at refluxing temperature for 1 hr. The resulting crystals were filtered off and the solvent was evaporated under reduced pressure to give 1.7 g of cis-4-aminomethyl-1-tert-butoxycarbonyl-3-hydroxypiperidine.

Workup

  1. temperatureat refluxing temperature for 1 hr
  2. filtrationThe resulting crystals were filtered off
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bd4fac9bf41f4bfa8ecdc9feee18d5e1
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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