Hydrochloric Acid → 2-Azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid, 5-methyl-, 2-(1,1-dimethylethyl) ester, (1R,3S,5R)-rel-

HRID 1527428Notes

Reaction equation

HRID 1527428 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][C@:10]2([CH3:12])[C@@H:8]([CH2:9]2)[N:7]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:5])C.[OH-].[K+].Cl.C(Cl)Cl>CO.C1COCC1.O>[C:16]([O:15][C:13]([N:7]1[C@H:6]([C:4]([OH:5])=[O:3])[CH2:11][C@:10]2([CH3:12])[C@H:8]1[CH2:9]2)=[O:14])([CH3:19])([CH3:17])[CH3:18]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 68283670HCID 68283670, compound

Product 1

HCID 583846722-Azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid, 5-methyl-, 2-(1,1-dimethylethyl) ester, (1R,3S,5R)-rel-

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1R,3S,5R)-5-methyl-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester (185 mg, 0.69 mmol) in MeOH (1.1 mL), THF (1.1 mL) and H2O (1.1 mL) was added KOH (77 mg, 1.37 mmol). The solution was stirred 2.5 h at RT, HCl (0.1N) was added (until pH 1), CH2Cl2 was added and the layers were separated (×2). The combined organic layers were dried (Na2SO4), filtered and concentrated. The material (yellow oil) thus obtained was used without further purification in the next step. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 12.46 (m, 1H), 3.86 (m, 1H), 3.06 (m, 1H), 2.40 (dd, 1H), 1.86 (m, 1H), 1.37 (m, 9H), 1.18 (s, 3H) 0.65 (m, 2H).

Workup

  1. additionwas added
  2. customthe layers were separated (×2)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe material (yellow oil) thus obtained
  7. customwas used without further purification in the next step

Sources & evidence

ORD record
ord-4a27fc7669864962a2d908a7659c6fda
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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