1-Butanamine, hydrofluoride → 3-(2,4-Dimethoxybenzyl)-5-hydroxymethyl-3-azabicyclo[3.1.0]hexan-2-one

HRID 83576

Reaction equation

HRID 83576 reaction equation
[Si]([O:8][CH2:9][C:10]12[CH2:15][CH:14]1[C:13](=[O:16])[N:12]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=1[O:26][CH3:27])[CH2:11]2)(C(C)(C)C)(C)C.[F-].C([NH3+])CCC>O1CCCC1>[CH3:27][O:26][C:19]1[CH:20]=[C:21]([O:24][CH3:25])[CH:22]=[CH:23][C:18]=1[CH2:17][N:12]1[CH2:11][C:10]2([CH2:9][OH:8])[CH:14]([CH2:15]2)[C:13]1=[O:16]

Participants

4

Reactant 2

HCID 536276511-Butanamine, hydrofluorideHCID 894658645-(Tert-butyldimethylsilanyloxymethyl)-3-(2,4-dimethoxybenzyl)-3-azabicyclo[3.1.0]hexan-2-one

Product 1

HCID 712879123-(2,4-Dimethoxybenzyl)-5-hydroxymethyl-3-azabicyclo[3.1.0]hexan-2-oneYield 91.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(tert-butyldimethylsilanyloxymethyl)-3-(2,4-dimethoxybenzyl)-3-azabicyclo[3.1.0]hexan-2-one (14.2 mg) in tetrahydrofuran (0.3 ml) was added n-butylammonium fluoride (54 μl, 1.0M solution in tetrahydrofuran) at room temperature, and the mixture was stirred for 1 hour. This reaction mixture was concentrated under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate, to chloroform/methanol=9/1) to give the titled compound (9.2 mg).

Workup

  1. concentrationThis reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate, to chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-e2d3ab0b0ea64d4e91bed6882736e9d1
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Linked notes

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