Water → (2S,4R)-N-t-butoxycarbonyl-4-t-butyldimethylsiloxy-2-(phenoxymethyl)pyrrolidine

HRID 725945Notes

Reaction equation

HRID 725945 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:10]([O:14][C:15]([N:17]1[CH2:21][C@H:20]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH2:19][C@H:18]1[CH2:30]OS(C)(=O)=O)=[O:16])([CH3:13])([CH3:12])[CH3:11].O>CN(C)C=O.C(OCC)(=O)C>[C:10]([O:14][C:15]([N:17]1[CH2:21][C@H:20]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:24])[CH3:25])[CH2:19][C@H:18]1[CH2:30][O:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 962WaterHCID 996PhenolHCID 24758Sodium hydrideHCID 14117008(2S,4R)-tert-butyl-4-(tert-butyldimethylsilyloxy)-2-((methylsulfonyloxy)methyl)pyrrolidine-1-carboxylate

Product 1

HCID 22881093(2S,4R)-N-t-butoxycarbonyl-4-t-butyldimethylsiloxy-2-(phenoxymethyl)pyrrolidineYield 60.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 300 mg, 7.50 mmol) was added to a solution of phenol (710 mg, 7.54 mmol) in N,N-dimethylformamide (10 ml). The resulting reaction solution was stirred at room temperature for 30 minutes and then a solution of (2S,4R)-N-t-butoxycarbonyl-4-t-butyldimethylsiloxy-2-(mesyloxymethyl)pyrrolidine (2.05 g, 5.00 mmol) in N,N-dimethylformamide (5 ml) was added thereto. The resulting liquid mixture was stirred at 70° C. overnight. The reaction solution was poured into a liquid mixture of water with ethyl acetate. The organic layer was washed with 1N aqueous potassium hydrogensulfate and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and then concentrated in Vacuo. The resulting residue was subjected to silica gel column chromatography (Wakogel™ C-300, heptane-ethyl acetate=4:1→1:1) to give (2S,4R)-N-t-butoxycarbonyl-4-t-butyldimethylsiloxy-2-(phenoxymethyl)pyrrolidine (1.23 g, yield 60%) as a pale yellow oily substance.

Workup

  1. customThe resulting reaction solution
  2. stirringThe resulting liquid mixture was stirred at 70° C. overnight
  3. washThe organic layer was washed with 1N aqueous potassium hydrogensulfate and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in Vacuo

Sources & evidence

ORD record
ord-561adcd412814c5ab3090b0f874d62fb
Source dataset
uspto-grants-1998_01
Patent number
US05707987

Reaction notes

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