1-(Aminomethyl)cyclohexan-1-ol → 1-Oxa-3-azaspiro[4.5]decan-2-one

HRID 1180575Notes

Reaction equation

HRID 1180575 reaction equation
[NH2:1][CH2:2][C:3]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[C:10]([O:14]C(OC(OC(C)(C)C)=O)=O)(C)(C)C>CN(C)C1C=CN=CC=1.C(#N)C.C(O)(=O)C.Cl>[O:9]1[C:3]2([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2)[CH2:2][NH:1][C:10]1=[O:14]

Participants

7

Reactant 2

HCID 776141-(Aminomethyl)cyclohexan-1-olHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 3490431-Oxa-3-azaspiro[4.5]decan-2-one

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolvent

Procedure

0.65 g (5.0 mmol) of 1-(aminomethyl)-cyclohexanol, 1.2 g (5.5 mmol) di-tert.-butyldicarbonate ((Boc)2O) and 0.611 g 4-dimethylaminopyridine were dissolved in 50 ml acetonitrile and agitated overnight at room temperature. The mixture was then fully turned over, the residue was dissolved in 20 ml acetic acid and again turned over. The residue was taken up in 25 ml 1 M hydrochloric acid and extracted with 50 ml toluene.

Workup

  1. extractionextracted with 50 ml toluene

Sources & evidence

ORD record
ord-7ac8cd96d6e54722932bd77cad796e30
Source dataset
uspto-grants-2007_10
Patent number
US07282515B2

Reaction notes

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