Ethanol → (-)-(S)-2,8-dimethyl-3-methylene-1-oxa-8-azaspiro[4.5]decane sesquifumarate

HRID 1653829Notes

Reaction equation

HRID 1653829 reaction equation
[CH3:1][C@H:2]1[C:6](=[CH2:7])[CH2:5][C:4]2([CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]2)[O:3]1.[C:14]([OH:21])(=[O:20])/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18].C(O)C>>[C:14]([OH:21])(=[O:20])/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18].[CH3:1][C@H:2]1[C:6](=[CH2:7])[CH2:5][C:4]2([CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]2)[O:3]1.[C:14]([OH:21])(=[O:20])/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18].[C:14]([OH:21])(=[O:20])/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18].[CH3:1][C@H:2]1[C:6](=[CH2:7])[CH2:5][C:4]2([CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]2)[O:3]1

Participants

4

Reactant 3

HCID 702EthanolHCID 444972Fumaric AcidHCID 6918122(S)-2,8-Dimethyl-3-methylene-1-oxa-8-azaspiro[4.5]decane

Product 1

HCID 131718954(-)-(S)-2,8-dimethyl-3-methylene-1-oxa-8-azaspiro[4.5]decane sesquifumarateYield 98.3%

Conditions

Temperature
4 °C

Procedure

To 70 ml of ethanol were added 24.39 g of (-)-(S)-2,8-dimethyl-3-methylene-1-oxa-8-azaspiro[4.5]decane and 27.3 g of fumaric acid and the mixture was heated to prepare a homogeneous solution. The solution was allowed to cool and maintained at 4° C. for about 15 hours. The resulting crystals were collected by filtration and dried under reduced pressure to give 47 g of (-)-(S)-2,8-dimethyl-3-methylene-1-oxa-8-azaspiro[4.5]decane sesquifumarate.

Workup

  1. temperaturethe mixture was heated
  2. customto prepare a homogeneous solution
  3. temperatureto cool
  4. filtrationThe resulting crystals were collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-cb86fa383352491ba0227d05c06df8c4
Source dataset
uspto-grants-1995_04
Patent number
US05403931

Reaction notes

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