Diethyl Ether → 4-Acetyl-2-(4-benzyloxyphenyl)-1-ethyl-7-hydroxymethylpyrrolo[2,1,5-cd]indolizine

HRID 1422112Notes

Reaction equation

HRID 1422112 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[N:14]3[C:9](=[C:10]([CH2:15][O:16][Si](C(C)(C)C)(C)C)[CH:11]=[CH:12][C:13]=13)[C:8]([CH2:24][CH3:25])=[C:7]2[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:28][CH:27]=1)(=[O:3])[CH3:2].O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C>O1CCCC1>[C:1]([C:4]1[CH:5]=[C:6]2[N:14]3[C:9](=[C:10]([CH2:15][OH:16])[CH:11]=[CH:12][C:13]=13)[C:8]([CH2:24][CH3:25])=[C:7]2[C:26]1[CH:27]=[CH:28][C:29]([O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[CH:30][CH:31]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 187070364-Acetyl-2-(4-benzyloxyphenyl)-7-(tert-butyldimethylsilanyloxymethyl)-1-ethylpyrrolo[2,1,5-cd]indolizine

Product 1

HCID 187070604-Acetyl-2-(4-benzyloxyphenyl)-1-ethyl-7-hydroxymethylpyrrolo[2,1,5-cd]indolizineYield 59.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Acetyl-2-(4-benzyloxyphenyl)-7-(tert-butyldimethylsilanyloxymethyl)-1-ethylpyrrolo[2,1,5-cd]indolizine (1.5 g, 2.79 mmol) and tetrabutylammoniumfluoride hydrate (2.92 g. 11.16 mmol) was dissolved in 20 ml of dry tetrahydrofuran and stirred for 24 hours. Diethyl ether (100 ml) was added and the organic layer was extracted with 100 ml of 15% acetic acid, 100 ml of saturated sodium hydrogen carbonate, 100 ml of water, washed with brine, dried over sodium sulfate, and evaporated to a red-brown solid. The crude product was purified by column chromatography over silica gel 60, using 10% of ethyl acetate in toluene as the eluent. Fractions containing the product were combined an the solvent was evaporated. The remaining solid was crystallised from toluene and petroleum ether to afford 0.7 g (59%) of the title compound. M.p. 190-191° C. MS(SP): m/z 423 (M+). 1H--NMR (DMSO-d6, 200 MHz) δ: 1.39 (t, 3 H); 2.64 (s, 3 H); 3.20 (q, 2 H); 5.18 (s, 2 H); 5.22 (s, 2 H); 7.25 (d, 2 H); 7.31-7.55 (m, 5 H); 7.75 (d, 2 H); 8.01 (d, 1 H); 8.20 (s, 1 H); 8.36 (d, 1 H). Analysis: Calculated for C28H25N1O3 : C, 79.41; H, 5.95; N, 3.31%; Found: C, 79.2; H, 5.7; N, 3.2%.

Workup

  1. extractionthe organic layer was extracted with 100 ml of 15% acetic acid, 100 ml of saturated sodium hydrogen carbonate, 100 ml of water
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated to a red-brown solid
  5. customThe crude product was purified by column chromatography over silica gel 60
  6. additionFractions containing the product
  7. customwas evaporated
  8. customThe remaining solid was crystallised from toluene and petroleum ether

Sources & evidence

ORD record
ord-fa295fceb28947ee9b7e2b4c16250184
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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