Ethyl diazoacetate → HCID 86690116, compound

HRID 520406Notes

Reaction equation

HRID 520406 reaction equation
[CH2:1]=[C:2]1[CH2:11][CH2:10][C:5]2(OCC[O:6]2)[CH2:4][CH2:3]1.[N+](=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N-]>C(Cl)Cl.C(O[Rh]OC(=O)C)(=O)C>[O:6]=[C:5]1[CH2:10][CH2:11][C:2]2([C@@H:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:1]2)[CH2:3][CH2:4]1

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetateHCID 109537438-Methylidene-1,4-dioxaspiro[4.5]decane

Product 1

HCID 86690116HCID 86690116, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 178476748HCID 178476748, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of diacetoxyrhodium (0.14 g, 0.317 mmol) and 8-methylene-1,4-dioxaspiro[4.5]decane (1.5 g, 9.73 mmol) in DCM (20 mL) was heated to reflux, and a solution of ethyl 2-diazoacetate (2.018 mL, 19.45 mmol) in DCM (6 mL) was added to it via syringe pump at 3.0 mL/h. The reaction mixture was stirred for 2 h after the completion of the addition, cooled to rt and concentrated. The residue was purified by silica gel chromatography (EtOAc/hexane) to afford ethyl (1S)-6-oxospiro[2.5]octane-1-carboxylate (1.9 g). 1H NMR (400 MHz, CDCl3) δ ppm 4.08-4.18 (2H, m), 3.94-3.99 (4H, m), 1.83 (4H, m), 1.59-1.67 (2H, m), 1.49-1.58 (2H, m), 1.35-1.46 (1H, m), 1.23-1.30 (3H, m), 1.15 (1H, t, J=4.89 Hz), 0.90 (1H, dd, J=7.91, 4.39 Hz).

Workup

  1. temperatureto reflux
  2. additionafter the completion of the addition
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-5153a590a29b48eea486ef42edb60e5a
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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