1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 131734832, compound

HRID 1778560Notes

Reaction equation

HRID 1778560 reaction equation
C([O:4][CH:5]1[CH2:10][CH:9]2[N:11]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[CH:6]1[CH2:7][C@H:8]2[C:22]([O:24][CH2:25][CH3:26])=[O:23])(=O)C.C1CCN2C(=NCCC2)CC1>CO>[OH:4][CH:5]1[CH2:10][CH:9]2[N:11]([C:12]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:13])[CH:6]1[CH2:7][C@H:8]2[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 131734833HCID 131734833, compound

Product 1

HCID 131734832HCID 131734832, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of O7-benzyl O5-ethyl (5R)-2-acetoxy-7-azabicyclo[2.2.1]heptane-5,7-dicarboxylate (0.87 g, 2.4 mmol) and DBU (0.73 g, 4.8 mmol) in methanol (20 mL) was stirred for 12 hours at room temperature. After removal of solvent, the residue was purified by silica gel chromatography to give O7-benzyl O5-ethyl (5R)-2-hydroxy-7-azabicyclo[2.2.1]heptane-5,7-dicarboxylate 151d. Yield: 45%. MS: calc'd (MH +) 306, measured (MH+) 306.

Workup

  1. customAfter removal of solvent
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f9f6d8e742c94bdd8b3a253b2647052e
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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