Hydrochloric Acid → (R)-6-Methyl-3-azabicyclo[3.2.0]heptane-1,3-dicarboxylic acid 3-benzyl ester

HRID 1917295Notes

Reaction equation

HRID 1917295 reaction equation
[OH-].[Na+].C[O:4][C:5]([C@:7]12[CH2:13][CH:12]([CH3:14])[CH:11]1[CH2:10][N:9]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH2:8]2)=[O:6].Cl>O1CCCC1.CO>[CH2:18]([O:17][C:15]([N:9]1[CH2:10][CH:11]2[C@:7]([C:5]([OH:6])=[O:4])([CH2:13][CH:12]2[CH3:14])[CH2:8]1)=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67491017(R)-6-Methyl-3-azabicyclo[3.2.0]heptane-1,3-dicarboxylic acid 3-benzyl ester 1-methyl ester

Product 1

HCID 67490768(R)-6-Methyl-3-azabicyclo[3.2.0]heptane-1,3-dicarboxylic acid 3-benzyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 1N sodium hydroxide solution (23 mL) was added dropwise to a mixed solution of (R)-6-methyl-3-azabicyclo[3.2.0]heptane-1,3-dicarboxylic acid 3-benzyl ester 1-methyl ester (3.5 g, 11.5 mmol) in tetrahydrofuran (60 mL) and methanol (20 mL) under ice-cooling, and the mixture was stirred for 30 minutes. The reaction solution was neutralized with 1N hydrochloric acid, followed by extraction with ethyl acetate. The extract was dried over magnesium sulfate and filtered. The solvent was evaporated under reduced pressure to give 3.4 g (quantitative) of the diastereomer mixture title compound as a colorless oil. The diastereomers were used for the next step without separation.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe extract was dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1000235a0d9a420cab8702599ea503ae
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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