Sodium Hydroxide → ethyl (6bR,10aS)-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate

HRID 1764799Notes

Reaction equation

HRID 1764799 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:22][CH2:21][C@@H:9]2[N:10]3[C:19]4[C:18]([C@@H:8]2[CH2:7]1)=[CH:17][CH:16]=[CH:15][C:14]=4[NH:13][C:12](=O)[CH2:11]3)=[O:5])[CH3:2].[OH-].[Na+]>Cl>[CH2:11]1[N:10]2[C@H:9]3[CH2:21][CH2:22][N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][C@H:8]3[C:18]3[C:19]2=[C:14]([CH:15]=[CH:16][CH:17]=3)[NH:13][CH2:12]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20578971ethyl (10R,15S)-3-oxo-1,4,12-triazatetracyclo[7.6.1.05,16.010,15]hexadeca-5,7,9(16)-triene-12-carboxylate

Product 1

HCID 86591143ethyl (6bR,10aS)-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To ethyl-(6bR,10aS)-2-oxo-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (4.41 g, 14.6 mmol) was added 1M BH3 THF complex solution (36.6 mL). The reaction was heated under reflux for 5 hr. After the reaction cooled down to r.t, 6N HCl ( 40 mL) was added dropwise with chilling. The reaction solution was heated under reflux for 30 minutes. After cooled down to r.t., 1N NaOH was added to adjust the pH to 8. The reaction was extracted with CH2Cl2 (2×200 mL). The combined organic layers were washed with brine, dried over MgSO4, and concentrated to afford ethyl (6bR,10aS)-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (4.10 g, 98%). The product was used in next step without further purification. MS-APcI: 288 [MH]+

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 5 hr
  3. temperatureAfter the reaction cooled down
  4. temperaturewith chilling
  5. temperatureThe reaction solution was heated
  6. temperatureunder reflux for 30 minutes
  7. extractionThe reaction was extracted with CH2Cl2 (2×200 mL)
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-9721395a7ead47379123ecce2b288cf0
Source dataset
uspto-grants-2007_06
Patent number
USRE039680E1

Reaction notes

Loading…