Water → tert-butyl(2S,4R)-2-[(dimethylamino)carbonyl]-4-(3-hydroxypropoxy)pyrrolidine-1-carboxylate

HRID 1662714

Reaction equation

HRID 1662714 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][O:12][C@H:13]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:15]([C:25]([N:27]([CH3:29])[CH3:28])=[O:26])[CH2:14]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[CH3:29][N:27]([CH3:28])[C:25]([C@@H:15]1[CH2:14][C@@H:13]([O:12][CH2:11][CH2:10][CH2:9][OH:8])[CH2:17][N:16]1[C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 67429248tert-butyl (2S,4R)-4-(3-{[tert-butyl(dimethyl)silyl]oxy}propoxy)-2-[(dimethylamino)carbonyl]pyrrolidine-1-carboxylate

Product 1

HCID 67428676tert-butyl(2S,4R)-2-[(dimethylamino)carbonyl]-4-(3-hydroxypropoxy)pyrrolidine-1-carboxylateYield 116%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2.10 g of the compound obtained in Step 139-1 in THF (100 ml) was added a solution 1 mol/L TBAF in THF (10 ml) under ice cooling and the reaction mixture was stirred at room temperature for two hours. Water was poured, the solution was extracted twice with CHCl3; the combined 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: CHCl3/MeOH=20/1 to 10/1; v/v) to obtain 1.79 g of the title compound.

Workup

  1. extractionthe solution was extracted twice with CHCl3
  2. washthe combined organic layer was washed with saturated brine
  3. dry with materialdried over MgSO4
  4. customthe drying agent was separated by filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by column chromatography (silicagel 60N; mobile phase: CHCl3/MeOH=20/1 to 10/1; v/v)

Sources & evidence

ORD record
ord-4550fb3c03414ae7a5b0e59b97e9ef18
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Linked notes

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