1-Butanol → HCID 68591606, compound

HRID 1876770Notes

Reaction equation

HRID 1876770 reaction equation
[CH3:1][N:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]3[C@@H:12]4[CH2:17][N:16](C([O-])=O)[CH2:15][CH2:14][C@@H:13]4[N:5]([C:6]=23)[CH2:4][CH2:3]1.[OH-].[K+].[CH2:23](O)[CH2:24]CC>>[CH2:23]([CH:4]1[N:5]2[C@H:13]3[CH2:14][CH2:15][NH:16][CH2:17][C@H:12]3[C:7]3[C:6]2=[C:11]([CH:10]=[CH:9][CH:8]=3)[N:2]([CH3:1])[CH2:3]1)[CH3:24]

Participants

4

Reactant 3

HCID 2631-ButanolHCID 14797Potassium HydroxideHCID 86641476HCID 86641476, compound

Product 1

HCID 68591606HCID 68591606, compound

Conditions

Temperature
120 °C

Procedure

(6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido-[3′,4′:4,5]-pyrrolo[1,2,3-de]quinoxaline-8-carboxylate (ca. 18.5 g, 57 mmol), KOH (12.7 g, 226 mmol) and n-butanol are placed in a 300 ml pressure bottle and heated in an oil bath at 120° C. for 3 hours. n-butanol is removed in vacuo and 300 ml of water is added and then extracted with DCM. The DCM layers are combined and washed with brine and dried (Na2SO4). Evaporation of the solvent gives (6bR,10aS)-ethyl-3-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido-[3′,4′:4,5]-pyrrolo[1,2,3-de]quinoxaline.

Workup

  1. customn-butanol is removed in vacuo and 300 ml of water
  2. additionis added
  3. extractionextracted with DCM
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-a908fb9662b84e04a5384706137cfcf1
Source dataset
uspto-grants-2012_11
Patent number
US08309722B2

Reaction notes

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