1-Butanol → HCID 68591606, compound

HRID 1624926Notes

Reaction equation

HRID 1624926 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-b957cb3126954774929ed9f4e36e1b2e
Source dataset
uspto-grants-2014_07
Patent number
US08779139B2

Reaction notes

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