Hydrochloric Acid → 8-Azabicyclo[3.2.1]octane-2,8-dicarboxylic acid, 8-(1,1-dimethylethyl) ester

HRID 594952Notes

Reaction equation

HRID 594952 reaction equation
[OH-].[K+].[CH:3]12[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:7]([CH2:8][CH2:9]1)[CH2:6][CH2:5][CH:4]2[C:18]([O:20]C)=[O:19].Cl>CO.O>[C:14]([O:13][C:11]([N:10]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH:4]([C:18]([OH:20])=[O:19])[CH2:5][CH2:6]2)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 580172018-(1,1-Dimethylethyl) 2-methyl 8-azabicyclo[3.2.1]octane-2,8-dicarboxylate

Product 1

HCID 668014908-Azabicyclo[3.2.1]octane-2,8-dicarboxylic acid, 8-(1,1-dimethylethyl) ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Potassium hydroxide (0.44 g, 7.8 mmol) was added into a solution of 8-tert-butyl 2-methyl 8-azabicyclo[3.2.1]octane-2,8-dicarboxylate (840 mg, 3.12 mmol) in methanol (2 ml) and water (2 ml). The reaction solution was stirred at room temperature for 16 h, and 1.0 N HCl solution was added dropwise to adjust pH to 4. The resulting solution was extracted with EtOAc (50 ml, twice). The combined organic layers were washed with water (10 ml). The organic layer was separated, and dried over sodium sulfate. The solution was filtered, concentrated, and used in the next step without further purification.

Workup

  1. extractionThe resulting solution was extracted with EtOAc (50 ml
  2. washThe combined organic layers were washed with water (10 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationThe solution was filtered
  6. concentrationconcentrated
  7. customused in the next step without further purification

Sources & evidence

ORD record
ord-40236d1e07144100b220e3a6b77e4e4d
Source dataset
uspto-grants-2016_01
Patent number
US09242981B2

Reaction notes

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