Sodium Hydroxide → N,N-dibenzyl-3-aminomethyltetrahydrofuran-2-one

HRID 2301001

Reaction equation

HRID 2301001 reaction equation
C([C:4]1([CH2:10][N:11]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7][O:6][C:5]1=[O:9])(=O)C.[OH-].[Na+]>[Cl-].C([N+](C)(C)CC1C=CC=CC=1)CCCCCCCCCCCCCCC.C(OCC)C>[CH2:12]([N:11]([CH2:10][CH:4]1[CH2:8][CH2:7][O:6][C:5]1=[O:9])[CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 102687063-acetyl-N,N-dibenzyl-3-aminomethyltetrahydrofuran-2-one

Product 1

HCID 18377523N,N-dibenzyl-3-aminomethyltetrahydrofuran-2-oneYield 58%

Reagents, catalysts & solvents 2

HCID 31202Benzylhexadecyldimethylammonium chlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

To 6.8 g of 3-acetyl-N,N-dibenzyl-3-aminomethyltetrahydrofuran-2-one, 33.8 g of diethyl ether and 0.68 g of cetyldimethylbenzylammonium chloride were added, followed by dropwise addition of 8 g of 10% by weight NaOH aqueous solution at 0° C. The resulting diethyl ether layer was separated, was concentrated under reduced pressure, the residue was subjected to column chromatography on a silica gel, was eluted with hexane-ethyl acetate and thereby yielded 3.45 g of N,N-dibenzyl-3-aminomethyltetrahydrofuran-2-one as a light yellow liquid.

Workup

  1. customThe resulting diethyl ether layer was separated
  2. concentrationwas concentrated under reduced pressure
  3. washwas eluted with hexane-ethyl acetate

Sources & evidence

ORD record
ord-0cb0cc847a3344d9b61ead87a49d5fac
Source dataset
uspto-grants-2002_12
Patent number
US06498258B2

Linked notes

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