Methanol → HCID 57164662, compound

HRID 1003254Notes

Reaction equation

HRID 1003254 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:18][CH2:17][CH2:16][C@:10]2([O:14][CH2:13][C:12](=C)[CH2:11]2)[C@@H:9]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[OH:26]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:18][CH2:17][CH2:16][C@:10]2([O:14][CH2:13][C:12](=[O:26])[CH2:11]2)[C@@H:9]1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 887MethanolHCID 57297718HCID 57297718, compound

Product 1

HCID 57164662HCID 57164662, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Through a cooled (-80° C.) solution of (6S,5R)-7-(tert-butoxycarbonyl)-3-methylene-6-phenyl-7-aza-1-oxa-spiro[4.5]decane (0.665 g; Desc.3) in dichloromethane (5 ml) and methanol (5 ml) was bubbled a mixture of ozone and oxygen for 0.75 hours. After the solution had been purged with nitrogen, dimethyl sulphide (0.5 ml) was added and then stirred under nitrogen at room temperature for 16 hours. The solvent was removed in vacuo and the residue partitioned between ethyl acetate and water. The organic phase was dried (MgSO4), evaporated and the residue purified by chromatography on silica gel elutintg with hexane containing increasing proportions of ethyl acetate between 0% to 10%. Evaporation of the fractions gave the title compound. MS (ES+) m/z 332 (M+H), 232 (M+2H-tBuOCO--), 276 (M+2H-tBu). 1H NMR (250 MHz, CDCl3) δ 7.58 (2H, d, J 6.2 Hz), 7.37-7.26 (3H, m), 5.3 (1H, s), 4.15 and 4.09 (2H, AB d, J 17.4 Hz), 3.97 (1H, m), 2.80 (1H, td, J 12.9 Hz and 4.0 Hz), 2.74 and 2.48 (2H, ABd, J 18.1 Hz), 2.29 (2H, m), 1.88-1.63 (2H, m), 1.44 (9H, s).

Workup

  1. customwas bubbled
  2. additiona mixture of ozone and oxygen for 0.75 hours
  3. customAfter the solution had been purged with nitrogen, dimethyl sulphide (0.5 ml)
  4. additionwas added
  5. customThe solvent was removed in vacuo
  6. customthe residue partitioned between ethyl acetate and water
  7. dry with materialThe organic phase was dried (MgSO4)
  8. customevaporated
  9. customthe residue purified by chromatography on silica gel elutintg with hexane containing
  10. temperatureincreasing proportions of ethyl acetate between 0% to 10%
  11. customEvaporation of the fractions

Sources & evidence

ORD record
ord-ae04a9156ff94b4b8a93cc011281af42
Source dataset
uspto-grants-2000_04
Patent number
US06046195

Reaction notes

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