Ammonium Chloride → HCID 86598901, compound

HRID 456749Notes

Reaction equation

HRID 456749 reaction equation
[OH:1][C@H:2]1[C@H:7]2[CH2:8][C@H:4]([C@@H:5]([C:16]([O:18][CH3:19])=[O:17])[N:6]2[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.C[O-].[Na+].[Cl-].[NH4+]>CO>[OH:1][C@H:2]1[C@H:7]2[CH2:8][C@H:4]([C@H:5]([C:16]([O:18][CH3:19])=[O:17])[N:6]2[C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:3]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 86598902HCID 86598902, compound

Product 1

HCID 86598901HCID 86598901, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 2-tert-butyl 3-methyl (1R,3S,4S,6R)-6-hydroxy-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylate (3.04 g), was added 1N sodiummethoxide solution in methanol (34 mL). The mixture was stirred at reflux for 4 hrs. To the resulting mixture was added ammonium chloride solution and evaporated in vacuo. Water was added to the residue, and the mixture was extracted with ethyl acetate. The combined organic phase was washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was recrystalized from hexane-diethyl ether to give the target compound (1.09 g) as a solid.

Workup

  1. temperatureat reflux for 4 hrs
  2. customevaporated in vacuo
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue was recrystalized from hexane-diethyl ether

Sources & evidence

ORD record
ord-0abc3035568c4e4e82e6aedd629e57c7
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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