Diazomethane → HCID 67490851, compound

HRID 1917412Notes

Reaction equation

HRID 1917412 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][C@@H:17]2[C@@:13]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])([CH2:14][C:15](=[CH2:19])[CH2:16]2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](=[CH2:30])=[N-]>C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:18][C@@H:17]2[C@@:13]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])([CH2:14][C:15]3([CH2:16]2)[CH2:30][CH2:19]3)[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 67491111HCID 67491111, compound

Product 1

HCID 67490851HCID 67490851, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

Palladium acetate (5.26 mg, 0.0234 mmol) was added to (1S,5R)-3-benzyloxycarbonyl-1-tert-butoxycarbonylamino-7-methylene-3-azabicyclo[3.3.0]octane (175 mg, 0.469 mmol) in diethyl ether (4.69 ml) in an open system under ice-cooling. The previously prepared solution of diazomethane in diethyl ether (20 ml) was slowly added to this solution under ice-cooling, and the mixture was stirred at room temperature for 16 hours. After filtration through Celite, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→95:5→90:10→88:12→87:13→86:14→85:15→83:17→80:20→75:25) to give 138 mg of the title compound as a transparent oil.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. filtrationAfter filtration through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→95:5→90:10→88:12→87:13→86:14→85:15→83:17→80:20→75:25)

Sources & evidence

ORD record
ord-a11fbaa9a31d4ccdb0dc86c7970417a1
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

Loading…