N-BOC-octahydroisoindole-1-carboxylic acid → octahydro-1H-isoindole-1-carboxylic acid

HRID 23876Notes

Reaction equation

HRID 23876 reaction equation
C([N:8]1[CH2:16][CH:15]2[CH:10]([CH2:11][CH2:12][CH2:13][CH2:14]2)[CH:9]1[C:17]([OH:19])=[O:18])(OC(C)(C)C)=O>Cl.O1CCOCC1>[CH:9]1([C:17]([OH:19])=[O:18])[CH:10]2[CH:15]([CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:16][NH:8]1

Participants

4

Reactant 1

HCID 22569207N-BOC-octahydroisoindole-1-carboxylic acid

Product 1

HCID 13207250octahydro-1H-isoindole-1-carboxylic acidYield 131.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

N-BOC-octahydroisoindole-1-carboxylic acid (18.6 mmol) was dissolved in 4 M HCl in dioxane (46.5 mL) at rt. After stirring for 1 hr, the reaction was determined to be complete by TLC. The reaction mixture was concentrated in vacuo, triturated with Et2O (2×70 mL) and then dried in vacuo to afford octahydroisoindole-1-carboxylic acid (4.13 g) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customtriturated with Et2O (2×70 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-71916f9f246848959ec6b6ef6ddfd45e
Source dataset
uspto-grants-2005_02
Patent number
US06855708B2

Reaction notes

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