Hydrochloric Acid → HCID 59752202, compound

HRID 750388Notes

Reaction equation

HRID 750388 reaction equation
[H-].[Na+].[Si:3]([O:10][CH:11]1[C:15]([CH3:17])([CH3:16])[CH2:14][NH:13][C:12]1=[O:18])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].Cl>O1CCCC1.[Cl-].[Na+].ClCCl>[Si:3]([O:10][CH:11]1[C:15]([CH3:17])([CH3:16])[CH2:14][N:13]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[C:12]1=[O:18])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 24758Sodium hydrideHCID 59752243HCID 59752243, compound

Product 1

HCID 59752202HCID 59752202, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 5234Sodium ChlorideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (39 mg, 0.97 mmol) was added to a solution of 3-{[tert-butyl(dimethyl)silyl]oxy}-4,4-dimethyl-2-pyrrolidinone (214 mg, 0.880 mmol) in anhydrous tetrahydrofuran (6 mL) under nitrogen at 0° C. After 10 min, benzyl chloroformate (0.200 mL, 1.32 mmol) was added, and the mixture was allowed to warm to room temperature. After 24 h, the mixture was diluted with saturated aqueous sodium chloride (30 mL) and dichloromethane (30 mL). Hydrochloric acid (10 mL, 1 N) was then added, and the two phases were separated. The aqueous layer was extracted with dichloromethane (35 mL), and the dichloromethane layers were combined. After washing with saturated aqueous sodium chloride, they were dried over magnesium sulfate and concentrated to a tan oil, which was further purified by column chromatography on silica gel. Elution with 10:1 hexane:ethyl acetate afforded benzyl 3-{[tert-butyl(dimethyl)silyl]oxy}-4,4-dimethyl-2-oxo-1-pyrrolidinecarboxylate as a colorless oil (312 mg, 94%). 1H NMR (300 MHz, DMSO-d6) δ 7.47-7.34 (m, 5H), 5.27 (1/2Abq, J=13 Hz, 1H), 5.21 (1/2Abq, J=13 Hz, 1H), 4.24 (s, 1H), 3.50 (1/2Abq, J=11 Hz, 1H), 3.38 (1/2Abq, J=11 Hz, 1H), 1.12 (s, 3H), 0.92 (s, 9H), 0.90 (s, 3H), 0.13 (s, 3H), 0.10 (s, 3H). ES-LCMS m/z 378 (M+H).

Workup

  1. waitAfter 24 h
  2. customthe two phases were separated
  3. extractionThe aqueous layer was extracted with dichloromethane (35 mL)
  4. washAfter washing with saturated aqueous sodium chloride, they
  5. dry with materialwere dried over magnesium sulfate
  6. concentrationconcentrated to a tan oil, which
  7. customwas further purified by column chromatography on silica gel
  8. washElution with 10:1 hexane

Sources & evidence

ORD record
ord-e379a1593de14310a87b8994e8a1b4cb
Source dataset
uspto-grants-2008_07
Patent number
US07402606B2

Reaction notes

Loading…