Pyridine → HCID 21112383, compound

HRID 2373519Notes

Reaction equation

HRID 2373519 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH:15]2[CH2:16][CH2:17][C:12]1([C:18]([OH:20])=O)[CH2:13][CH2:14]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:21]1C=CC=CC=1.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.C(=O)(O)[O-].[NH4+]>O1CCOCC1>[NH2:21][C:18]([C:12]12[N:11]([C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])[CH:15]([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=[O:20]

Participants

6

Reactant 4

HCID 1049PyridineHCID 14013Ammonium BicarbonateHCID 90495Di-tert-butyl dicarbonateHCID 10612438HCID 10612438, compound

Product 1

HCID 21112383HCID 21112383, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stirred solution of 7-[(benzyloxy)carbonyl]-7-azabicyclo[2.2.1]heptane-1-carboxylic acid (C-35) in dioxane was treated with pyridine (0.8 eq.) and Boc2O (1.5 eq.), then ammonium bicarbonate (1.46 eq.) was added and the mixture was stirred at room temperature for 15 hours. Dioxane was concentrated and the residue was taken up in ethyl acetate, washed with HCl 1N and brine and dried over Na2SO4 to give, after filtration and concentration, the titled compound (C-36).

Workup

  1. concentrationDioxane was concentrated
  2. washwashed with HCl 1N and brine
  3. dry with materialdried over Na2SO4
  4. customto give
  5. filtrationafter filtration and concentration

Sources & evidence

ORD record
ord-a5b5bc703b8742ee807d485bbc4af769
Source dataset
uspto-grants-2008_12
Patent number
US07459452B2

Reaction notes

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