Water → tert-butyl (2S,4R)-4-(3-{[tert-butyl(dimethyl)silyl]oxy}propoxy)-2-[(dimethylamino)carbonyl]pyrrolidine-1-carboxylate

HRID 1662713Notes

Reaction equation

HRID 1662713 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:20])[C:5]([C@@H:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][N:8]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:6].ICCC[Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].O.[CH2:33]1C[O:36][CH2:35][CH2:34]1>>[Si:25]([O:36][CH2:35][CH2:34][CH2:33][O:12][C@H:10]1[CH2:9][N:8]([C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[C@H:7]([C:5]([N:4]([CH3:20])[CH3:3])=[O:6])[CH2:11]1)([C:28]([CH3:29])([CH3:30])[CH3:31])([CH3:26])[CH3:27]

Participants

6

Reactant 5

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 15261805HCID 15261805, compoundHCID 67430109tert-butyl (2S,4S)-2-(dimethylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 67429248tert-butyl (2S,4R)-4-(3-{[tert-butyl(dimethyl)silyl]oxy}propoxy)-2-[(dimethylamino)carbonyl]pyrrolidine-1-carboxylate

Conditions

Temperature
50 °C

Procedure

Under nitrogen atmosphere, to a suspension of 1.55 g of NaH in THF (100 ml) was added 10.0 g of tert-butyl (2S,4S)-2-[(dimethylamino)carbonyl]-4-hydroxypyrrolidine-1-carboxylate and the reaction mixture was stirred at 50° C. for one hour. Thereafter, at the same temperature, solution of 23.2 g of (3-iodopropyl)-tert-butyl-dimethyl silane in THF (10 ml) was added, and the solution was refluxed for two hours. The solution was poured into water and the resulting mixture was extracted with EtOAc; the organic layer was washed with saturated brine and dried over MgSO4, then, the drying agent was separated by filtration and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silicagel 60N; mobile phase: n-hexane/EtOAc=1/1 to 0/1; v/v) to obtain 2.10 g of the title compound.

Workup

  1. temperaturethe solution was refluxed for two hours
  2. extractionthe resulting mixture was extracted with EtOAc
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over MgSO4
  5. customthe drying agent was separated by filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by column chromatography (silicagel 60N; mobile phase: n-hexane/EtOAc=1/1 to 0/1; v/v)

Sources & evidence

ORD record
ord-ef4262beb1b746b1a18a80a9c364d842
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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