Magnesium monoxide → 2-Oxa-4-azatetracyclo[6.3.1.16,10.01,5]tridecan-3-one

HRID 2092024

Reaction equation

HRID 2092024 reaction equation
[C:1](=[O:14])([O:3][C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([CH2:7]3)[CH2:5]1)[CH2:11]2)[NH2:2].IC1C=CC=C(CC([O-])=O)C=1CC([O-])=O.[O-2].[Mg+2]>ClCCl.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[C:4]123[CH2:5][CH:6]4[CH2:12][CH:10]([CH2:9][CH:8]([CH2:7]4)[CH:13]1[NH:2][C:1](=[O:14])[O:3]2)[CH2:11]3

Participants

6

Reactant 3

HCID 6850729Magnesium monoxideHCID 124376461-Adamantyl carbamateHCID 219456882-[2-(Carboxylatomethyl)-3-iodophenyl]acetate

Product 1

HCID 28074452-Oxa-4-azatetracyclo[6.3.1.16,10.01,5]tridecan-3-oneYield 77%

Reagents, catalysts & solvents 2

HCID 423677Acetic acid, rhodium salt (4:2)CatalystHCID 6344DichloromethaneSolvent

Procedure

Tricyclo[3.3.1.13,7]dec-1-yl carbamate (100 mg, 0.512 mmol), iodobenzenediacetate (220 mg, 0.683 mmol), magnesium oxide (50 mg, 1.24 mmol) and rhodium (II) acetate dimer (22 mg, 0.050 mmol) were stirred in dichloromethane (3 mL) at 50° C. for 5 hours. After completion of the reaction, the reaction solution was filtered, and the solid was washed with chloroform and the filtrate was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1→2/1) to give the desired product (77% yield).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction solution was filtered
  3. washthe solid was washed with chloroform
  4. customthe filtrate was evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1→2/1)

Sources & evidence

ORD record
ord-d4ce184fdb4f48e6b71ded0bd1b8f1ab
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Linked notes

Loading…