HCID 86753637, compound → tert-Butyl (3S,4R)-4-(aminomethyl)-3-methoxypiperidine-1-carboxylate

HRID 344293Notes

Reaction equation

HRID 344293 reaction equation
[N:1]([CH2:4][C@H:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][C@H:6]1[O:18][CH3:19])=[N+]=[N-]>CO.[OH-].[C+4].[Pd+2].[OH-].[OH-].[OH-].[OH-].[OH-]>[NH2:1][CH2:4][C@H:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:7][C@H:6]1[O:18][CH3:19]

Participants

4

Reactant 1

HCID 86753637HCID 86753637, compound

Product 1

HCID 70074677tert-Butyl (3S,4R)-4-(aminomethyl)-3-methoxypiperidine-1-carboxylateYield 88.5%

Reagents, catalysts & solvents 2

HCID 178420936HCID 178420936, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of cis-4-azidomethyl-1-tert-butoxycarbonyl-3-methoxypiperidine (1.5 g) in methanol (50 ml) was added 20% palladium carbon hydroxide (0.6 g), and the resulting mixture was stirred at room temperature under hydrogen atmosphere for 2 hr. 20% Palladium carbon hydroxide was filtered off and the solvent was evaporated under reduced pressure to give 1.2 g of cis-4-aminomethyl-1-tert-butoxycarbonyl-3-methoxypiperidine.

Workup

  1. filtration20% Palladium carbon hydroxide was filtered off
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d48448f9f14e4c21a299ed8e1280016a
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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