HCID 69014270, compound → HCID 69015024, compound

HRID 1436523Notes

Reaction equation

HRID 1436523 reaction equation
C([O:3][C:4]([CH:6]1[CH:11]2[CH:12]([CH2:13][O:14][CH3:15])[CH:8]([CH2:9][CH2:10]2)[N:7]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=O)C>ClCCl>[C:19]([O:18][C:16]([N:7]1[CH:6]([CH2:4][OH:3])[CH:11]2[CH:12]([CH2:13][O:14][CH3:15])[CH:8]1[CH2:9][CH2:10]2)=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

3

Reactant 1

HCID 69014270HCID 69014270, compound

Product 1

HCID 69015024HCID 69015024, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add di-isobutylalluminium hydrate (1 M in hexanes, 14.6 mL, 14.6 mmol) to a solution of 7-methoxymethyl-2-aza-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester (1.53 g, 4.88 mmol) in dichloromethane (20 mL) cooled in an ice bath. Stir the mixture at room temperature for 3 h. Quench with saturated aqueous sodium tartrate and stir until the solution becomes clear. Extract the mixture with ethyl acetate (3×50 mL), wash the combined extract with saturated aqueous sodium tartrate, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 1:1 ethyl acetate:hexanes) to give the title compound (0.780 g, 59%).

Workup

  1. temperaturecooled in an ice bath
  2. customQuench with saturated aqueous sodium tartrate
  3. stirringstir until the solution
  4. extractionExtract the mixture with ethyl acetate (3×50 mL)
  5. washwash the
  6. extractioncombined extract with saturated aqueous sodium tartrate
  7. dry with materialdry (magnesium sulfate)
  8. concentrationconcentrate
  9. custompurify
  10. wash(silica gel chromatography, eluting with 1:1 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-cd447df8c870440ea329e5ab7ff4cbd3
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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