Pyridine → HCID 67264027, compound

HRID 1686969Notes

Reaction equation

HRID 1686969 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C@@H:14]2[CH2:15][C@@H:11]([CH:12]=[CH:13]2)[C@@H:10]1[C:16]([OH:18])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(OC(OC(C)(C)C)=O)=O)(C)(C)C.[N:34]1C=CC=CC=1.O1CCOCC1.C(=O)(O)[O-].[NH4+]>>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[C@@H:10]([C:16](=[O:18])[NH2:34])[C@H:11]2[CH2:15][C@@H:14]1[CH:13]=[CH:12]2)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 5

HCID 1049PyridineHCID 14013Ammonium BicarbonateHCID 312751,4-DioxaneHCID 90495Di-tert-butyl dicarbonateHCID 10934012HCID 10934012, compound

Product 1

HCID 67264027HCID 67264027, compoundYield 97.5%

Procedure

(1S,2S,3R,4R)-3-tert-Butoxycarbonylamino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (6.66 g, 26.3 mmol), Di-tert-Butyldicarbonate (8.6 g, 39 mmol) and Pyridine (3.8 mL, 47 mmol) were added to 1,4-Dioxane (40 mL, 500 mmol) and the reaction stirred for 30 minutes at room temperature. Ammonium Bicarbonate (5.8 g, 74 mmol) was added, and the reaction mixture was stirred overnight. The reaction was quenched by addition of water. Extraction (2×) with EtOAc, washing 2× with 0.1 N HCl, and once w/ brine, drying (MgSO4), concentration, provided ((1R,2R,3S,4S)-3-Carbamoyl-bicyclo[2.2.1]hept-5-en-2-yl)-carbamic acid tert-butyl ester as a white solid (6.47 grams).

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. customThe reaction was quenched by addition of water
  3. extractionExtraction (2×) with EtOAc
  4. washwashing 2× with 0.1 N HCl
  5. customdrying
  6. concentration(MgSO4), concentration

Sources & evidence

ORD record
ord-0e976273e6cb4350bb17462dee5824cd
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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