Methanol → HCID 21912718, compound

HRID 1245594Notes

Reaction equation

HRID 1245594 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:21])[C:15](=[N+]=[N-])[C:16](=[O:18])[CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22][OH:23]>CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:21])[CH:15]([O:23][CH3:22])[C:16](=[O:18])[CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 73853093HCID 73853093, compound

Product 1

HCID 21912718HCID 21912718, compound

Reagents, catalysts & solvents 1

HCID 423677Acetic acid, rhodium salt (4:2)Catalyst

Conditions

Temperature
65 °C

Procedure

A solution of 532 mg (1.8 mmol) of 1-(tert-butoxycarbonyl)-4-(2-diazo-1,3-dioxo-but-1-yl)piperidine in 5 mL of MeOH was treated with 25 mg (0.056 mmol) of rhodium (II) acetate dimer. The reaction was slowly warmed to 65° C. over 2 hours. Upon cooling, volatiles were removed under reduced pressure. The residue was partitioned between 100 mL of EtOAc and 100 mL of H2O. After separating phases, the organic layer was washed with 100 mL of brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography using 19:1 v/v hexanes/acetone as the eluant to afford the title compound as a yellow oil: RF: 0.39 (4:1 v/v hexanes/acetone); 1H-NMR (500 MHz) δ 1.45, 1.47 (2s, 9H), 1.68–1.71 (m, 3H), 2.19, 2.22 (2s, 3H), 2.78–2.89 (m, 2H), 3.44, 3.58 (2s, 3H), 4.03–4.3 (m, 2H).

Workup

  1. temperatureUpon cooling
  2. customvolatiles were removed under reduced pressure
  3. customThe residue was partitioned between 100 mL of EtOAc and 100 mL of H2O
  4. customAfter separating phases
  5. washthe organic layer was washed with 100 mL of brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-68d81844e6e2457b9d09cd8ae01eeca0
Source dataset
uspto-grants-2006_10
Patent number
US07125887B2

Reaction notes

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