Hydrochloric Acid → 4-Aminobicyclo[2.2.1]heptane-1-carboxylic acid

HRID 2280792Notes

Reaction equation

HRID 2280792 reaction equation
C(OC([NH:11][C:12]12[CH2:18][C:15]([C:19]([OH:21])=[O:20])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=O)C1C=CC=CC=1.CO.Cl.[H][H]>[Pd].CO.C(OCC)(=O)C>[NH2:11][C:12]12[CH2:18][C:15]([C:19]([OH:21])=[O:20])([CH2:14][CH2:13]1)[CH2:16][CH2:17]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 574674274-(((Benzyloxy)carbonyl)amino)bicyclo[2.2.1]heptane-1-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 450848204-Aminobicyclo[2.2.1]heptane-1-carboxylic acidYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A 2-L Parr bottle was charged with 4-(benzyloxycarbonylamino)bicyclo[2.2.1]heptane-1-carboxylic acid (105 g, 363 mmol), methanol (500 mL), 0.8 N hydrochloric acid (500 mL), and 10% palladium on carbon (38.6 g, 18.15 mmol, 50% wet with water). The reaction mixture was reacted on a Parr shaker under 30 gpsi hydrogen for 10 h when TLC analysis (10% methanol/ethyl acetate) indicated a complete reaction. The catalyst was removed by filtration through a short plug of celite and the plug was washed thoroughly with water (4×100 mL). The filtrate was concentrated to provide 4-aminobicyclo[2.2.1]heptane-1-carboxylic acid (56.3 g, 100%) as a wet white solid which was used in the next step without any further purification; MS (ESI) m/z 156.2 [M+1]+

Workup

  1. customa complete reaction
  2. customThe catalyst was removed by filtration through a short plug of celite
  3. washthe plug was washed thoroughly with water (4×100 mL)
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f0d2e5dd5e694a07be573ad9ef97b840
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

Loading…