Tetrahydrofuran → HCID 67696277, compound

HRID 1656110Notes

Reaction equation

HRID 1656110 reaction equation
[Li][CH2:2][CH2:3]CC.[S:6]([N:16]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:18]([CH2:19][CH2:20][N:21]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:17]1)([C:9]1[CH:15]=[CH:14][C:12]([CH3:13])=[CH:11][CH:10]=1)(=[O:8])=[O:7].[C:42](=[O:44])=O.[CH3:45]C(C)=O.C(C1C=C2[C:57](=[CH:58]C=1)[N:56](C)[CH:55]1[CH2:61][N:62]([CH3:65])[CH2:63][CH2:64][CH:54]21)=O.[CH2:66]1[CH2:70]O[CH2:68][CH2:67]1>CO>[CH2:65]([N:62]1[CH2:63][CH2:64][CH:54]2[CH:55]([N:56]([CH2:57][CH3:58])[C:66]3[C:70]2=[CH:3][C:2]([C:17]2[N:16]([S:6]([C:9]4[CH:15]=[CH:14][C:12]([CH3:13])=[CH:11][CH:10]=4)(=[O:7])=[O:8])[C:41]4[C:36]([C:18]=2[CH2:19][CH2:20][N:21]([CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:37][CH:38]=[CH:39][CH:40]=4)=[CH:68][CH:67]=3)[CH:61]1[CH2:42][OH:44])[CH3:45]

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 18522661Acetone cardiceHCID 19789761HCID 19789761, compoundHCID 19789781HCID 19789781, compoundHCID 178418339Butyllithium

Product 1

HCID 67696277HCID 67696277, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.18 ml of n-BuLi (15% hexane) were added under ice-cooling to a solution of 1-tosyl-N,N-dibenzyltryptamine (1.72 g) in anhydrous THF, which was cooled with dry ice-acetone. 6-Formyl-2,9-dimethyl-1,2,3,4,4a,9a-hexahydropyrido[3,4-b]indole (0.6 g) was added and the mixture stirred for 4 hrs. Methanol was added and the solvent was removed by evaporation from the reaction solution. The residue to which water was added was extracted with ethyl acetate. The ethyl acetate layer was washed with water and then brine, dried over magnesium sulfate. The crude product was purified by column chromatography on silica gel. Eluates with 3% methanol/chloroform gave 1.15 g of the title compound.

Workup

  1. customthe solvent was removed by evaporation from the reaction solution
  2. additionThe residue to which water was added
  3. extractionwas extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialbrine, dried over magnesium sulfate
  6. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0d5ad7c26b444e2b8e9b53975724b269
Source dataset
uspto-grants-1993_10
Patent number
US05252580

Reaction notes

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