Water → HCID 19914904, compound

HRID 1650282Notes

Reaction equation

HRID 1650282 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH:11]([CH2:12][O:13][CH3:14])[CH2:10][CH2:9][CH:8]1[CH2:15][O:16][Si](C(C)(C)C)(C)C)=[O:6])[CH:2]=[CH2:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C>O1CCCC1>[CH2:1]([O:4][C:5]([N:7]1[CH:11]([CH2:12][O:13][CH3:14])[CH2:10][CH2:9][CH:8]1[CH2:15][OH:16])=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 54256610HCID 54256610, compound

Product 1

HCID 19914904HCID 19914904, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-allyloxycarbonyl-2-t-butyldimethylsilyloxymethyl-5-methoxymethylpyrrolidine (9.67 g) in tetrahydrofuran (97 ml) was added dropwise a solution of tetrabutylammonium fluoride in tetrahydrofuran (31 ml) at 0° C. The mixture was allowed to warm to room temperature and stirred for an hour. The mixture was poured into water and ethyl acetate, and the aqueous layer was separated and extracted twice with ethyl acetate. The combined organic layer was washed twice with 1N hydrochloric acid, and with saturated aqueous sodium bicarbonate, water and brine successively, dried over magnesium sulfate and evaporated under reduced pressure to give 1-allyloxycarbonyl-2-hydroxymethyl-5-methoxymethylpyrrolidine (5.60 g).

Workup

  1. customthe aqueous layer was separated
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layer was washed twice with 1N hydrochloric acid
  4. dry with materialwith saturated aqueous sodium bicarbonate, water and brine successively, dried over magnesium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4f5f6b81203f404baaeea7da72f13c60
Source dataset
uspto-grants-1990_05
Patent number
US04923857

Reaction notes

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