Hydrochloric Acid → HCID 11439682, compound

HRID 1374434Notes

Reaction equation

HRID 1374434 reaction equation
COC[O:4][CH2:5][C@@H:6]1[C:10]([C:11]([O:13][C:14](C)(C)C)=[O:12])=[CH:9][CH2:8][N:7]1[C:18]([O:20][CH2:21][CH:22]=[CH2:23])=[O:19].Cl.CO.N1C(C)=CC=CC=1C.[Si:35](OS(C(F)(F)F)(=O)=O)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36].C[Si](C=[N+]=[N-])(C)C.CCCCCC.Cl>CO.C1(C)C=CC=CC=1>[Si:35]([O:4][CH2:5][C@@H:6]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH2:8][N:7]1[C:18]([O:20][CH2:21][CH:22]=[CH2:23])=[O:19])([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36]

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 79372,6-LutidineHCID 8058HexaneHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 167693TrimethylsilyldiazomethaneHCID 21893726Hydrochloride methanolHCID 86592531HCID 86592531, compound

Product 1

HCID 11439682HCID 11439682, compoundYield 22.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 1-allyl 3-tert-butyl (2S)-2-[(methoxymethoxy)methyl]-2,5-dihydro-1H-pyrrole-1,3-dicarboxylate (296 mg, 0.90 mmol) in methanol (2 ml) was added hydrochloric acid/methanol(5 ml) and the mixture was stirred overnight. To the solution was added toluene and the solvent was removed in vacuo. To the residue were added methanol and toluene and the solvent was again removed in vacuo. The residue was dissolved in THF (8 ml) and thereto were added at 0–5° C. 2,6-lutidine (0.84 ml, 7.2 mmol) and tert-butyldimethylsilyltriflate (0.83 ml, 3.6 mmol). The mixture was stirred at room temperature for 1 hour and thereto was added at 0–5° C. a solution of trimethylsilyldiazomethane in hexane (2M, 0.45 ml, 0.90 mmol). Thirty minutes later the mixture was raised to room temperature and stirred for 30 minutes. Thirty minutes later to the mixture were added 1N hydrochloric acid and a saturated aqueous sodium chloride solution, and the mixture was separated with a separating funnel. The organic layer was dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was purified with silica gel (26 g) chromatography (hexane/ethyl acetate=1/5) to give 1-allyl 3-methyl (2S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,5-dihydro-1H-pyrrole-1,3-dicarboxylate (71 mg, 22%).

Workup

  1. customthe solvent was removed in vacuo
  2. additionTo the residue were added methanol and toluene
  3. customthe solvent was again removed in vacuo
  4. dissolutionThe residue was dissolved in THF (8 ml)
  5. additionwere added at 0–5° C
  6. stirringThe mixture was stirred at room temperature for 1 hour
  7. stirringstirred for 30 minutes
  8. customa saturated aqueous sodium chloride solution, and the mixture was separated with a separating funnel
  9. dry with materialThe organic layer was dried over magnesium sulfate
  10. customthe solvent was removed in vacuo
  11. customThe residue was purified with silica gel (26 g) chromatography (hexane/ethyl acetate=1/5)

Sources & evidence

ORD record
ord-0236af9c3d0c469b88deff738c980b2a
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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