Water → HCID 19914920, compound

HRID 1650281Notes

Reaction equation

HRID 1650281 reaction equation
[CH2:1]([N:8]1[CH:12]([CH2:13][OH:14])[CH2:11][CH2:10][CH:9]1[CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:26]I.O>O1CCCC1.C(OCC)(=O)C>[CH2:1]([N:8]1[CH:12]([CH2:13][O:14][CH3:26])[CH2:11][CH2:10][CH:9]1[CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])[CH3:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19914911HCID 19914911, compound

Product 1

HCID 19914920HCID 19914920, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-benzyl-2-t-butyldimethylsilyloxymethyl-5-hydroxymethylpyrrolidine (10 g) in tetrahydrofuran (100 ml) was added portionwise sodium hydride (2.3 g) at 0° C. The mixture was stirred at the same temperature for 30 minutes. And then methyl iodide was added to the mixture. After stirring for an hour at room temperature, water and ethyl acetate was added thereto. The aqueous layer was separated and washed twice with ethyl acetate. The combined organic layer was washed with saturated aqueous sodium hydrogen carbonate, water and brine successively, dried over magnesium sulfate and evaporated under reduced pressure to give 1-benzyl-2-t-butyldimethylsilyloxymethyl-5-methoxymethylpyrrolidine (9.99 g).

Workup

  1. stirringAfter stirring for an hour at room temperature
  2. customThe aqueous layer was separated
  3. washwashed twice with ethyl acetate
  4. washThe combined organic layer was washed with saturated aqueous sodium hydrogen carbonate, water and brine successively
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-715f83ca5e014700aa390cfc906cff5c
Source dataset
uspto-grants-1990_05
Patent number
US04923857

Reaction notes

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