Salicylic Acid → (3aS-cis)-6-Formyl-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol salicylate hemihydrate

HRID 2081973Notes

Reaction equation

HRID 2081973 reaction equation
[CH3:1][C@:2]12[C:9]3[CH:10]=[C:11]([OH:14])[CH:12]=[CH:13][C:8]=3[N:7]([CH3:15])[C@H:6]1[N:5]([CH3:16])[CH2:4][CH2:3]2.[C:17]([OH:26])(=[O:25])[C:18]1[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=1)[OH:20].[CH2:27]([OH:29])[CH3:28]>[OH-].[Na+].CCOCC>[OH2:14].[C:17]([O:26][C:11]1[CH:10]=[C:9]2[C:8](=[CH:13][C:12]=1[CH:27]=[O:29])[N:7]([CH3:15])[C@H:6]1[N:5]([CH3:16])[CH2:4][CH2:3][C@@:2]21[CH3:1])(=[O:25])[C:18]1[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=1)[OH:20].[CH:27]([C:28]1[CH:13]=[C:8]2[C:9]([C@:2]3([CH3:1])[CH2:3][CH2:4][N:5]([CH3:16])[C@@H:6]3[N:7]2[CH3:15])=[CH:10][C:11]=1[O:25][C:17](=[O:26])[C:18]1[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=1)[OH:20])=[O:29]

Participants

6

Reactant 3

HCID 338Salicylic AcidHCID 702EthanolHCID 119198Eseroline

Product 1

HCID 131717747(3aS-cis)-6-Formyl-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol salicylate hemihydrate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
45 °C

Procedure

A solution prepared from 6-formyl-N,N-diethylcarbamate ester of eseroline (960 mg) in ethanol (20 ml) and 10% NaOH (10 ml) was degassed and heated at 45° C. for 30 minutes. The solution was poured into degassed sodium bicarbonate solution (15 ml) and extracted with ethyl acetate (3×150 ml). The ethyl acetate solution was washed with brine (150 ml), dried over MgSO4, and concentrated to an oil. Purification was effected by flash chromatography over silica gel using 1% CH3OH/DCM. The pure product thus obtained weighed 722 mg as an oil. The oil was dissolved in ether (15 ml) and treated with a solution of salicylic acid (405 mg) in ether (20 ml). The crystalline product weighed 1.04 g, mp 156°-157° C.

Workup

  1. customwas degassed
  2. additionThe solution was poured
  3. custominto degassed sodium bicarbonate solution (15 ml)
  4. extractionextracted with ethyl acetate (3×150 ml)
  5. washThe ethyl acetate solution was washed with brine (150 ml)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to an oil
  8. customPurification
  9. customThe pure product thus obtained

Sources & evidence

ORD record
ord-c3773d36e49f4b84800df60fba42df13
Source dataset
uspto-grants-1993_02
Patent number
US05187165

Reaction notes

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