tert-butyl 5-(benzylamino)-4-methylhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate → tert-butyl 5-amino-4-methylhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

HRID 877692Notes

Reaction equation

HRID 877692 reaction equation
C([NH:8][CH:9]1[CH2:23][CH:12]2[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH:11]2[CH:10]1[CH3:24])C1C=CC=CC=1.[H][H]>[OH-].[OH-].[Pd+2]>[NH2:8][CH:9]1[CH2:23][CH:12]2[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:15][CH:11]2[CH:10]1[CH3:24]

Participants

4

Reactant 2

HCID 68290857tert-butyl 5-(benzylamino)-4-methylhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 68291516tert-butyl 5-amino-4-methylhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylateYield 107.4%

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

A mixture of tert-butyl 5-(benzylamino)-4-methylhexahydrocyclopenta-[c]pyrrole-2(1H)-carboxylate (13.2 g, 39.9 mmol) and 20% palladium hydroxide on carbon (4.21 g, 5.99 mmol) was stirred under 30 psi hydrogen for 5 h. The mixture was filtered through a celite pad to remove the solid catalyst. The filter cake was rinsed with methanol. The filtrate was concentrated to give crude tert-butyl 5-amino-4-methylhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (10.3 g) as an approximately 3:1:1 mixture of three isomers. The material was taken to the next step without further purification. MS (ES+) m/z: 241.2 (M+H).

Workup

  1. filtrationThe mixture was filtered through a celite pad
  2. customto remove the solid catalyst
  3. washThe filter cake was rinsed with methanol
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8ab1a948bb544bf48b04dc8b1660665a
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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