Pyridine → HCID 67264027, compound

HRID 1040661Notes

Reaction equation

HRID 1040661 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-a95444853b6e44a08693b87140cd2ed5
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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