Water → HCID 18707037, compound

HRID 1422081Notes

Reaction equation

HRID 1422081 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[N:13]3[C:17]=1[CH:16]=[C:15]([C:18](OCC)=[O:19])[C:14]3=[C:23]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:29][CH:28]=1)[C:24]=2[CH2:25][CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(OCC)C>O1CCCC1>[CH2:1]([O:8][C:9]1[C:17]2[N:13]3[C:12](=[CH:11][CH:10]=1)[C:24]([CH2:25][CH3:26])=[C:23]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)=[CH:29][CH:28]=1)[C:14]3=[C:15]([CH2:18][OH:19])[CH:16]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 18707007HCID 18707007, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18707037HCID 18707037, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 7-benzyloxy-3-(4-benzyloxyphenyl)-4-ethylpyrrolo[2,1,5-cd]indolizine-2-carboxylate (15.79 g, 30 mmol) was dissolved in 250 ml of dry tetrahydrofuran under a nitrogen atmosphere. Lithium aluminium hydride (1.8 g, 50 mmol) was added in small portions, and the mixture was stirred at room temperature for 21/2 hours. Water was added until effervescence terminated and solid potassium carbonate was added until a white suspension was formed. Diethyl ether (200 ml) was added and the reaction mixture was stirred vigorously. The reaction mixture was filtered through celite and the organic material was extracted into 3×100 ml of diethyl ether and 3×100 ml of ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and the solvent was evaporated. The crude product was recrystallized from hot ethyl acetate and petroleum ether. This gave 13.06 g (89%) of 5-benzyloxy-2-(4-benzyloxyphenyl)-1-ethyl-3-hydroxymethyl-pyrrolo[2,1,5-cd]indolizine as yellow crystals. M.p. 133-134° C. MS(SP): m/z 487 (M+). 1H-NMR (DMSO-d6, 400 MHz) δ: 1.34 (t, 3H); 3.04 (q, 2H); 4.81 (s, 2H); 5.18 (m, 3H); 5.57 (s, 2H); 7.20 (d, 2H); 7.31-7.64 (m, 14H); 7.92 (d, 1H). The structure has been proven by COSY, ROESY and NOESY, 400 MHz.

Workup

  1. customterminated
  2. additionsolid potassium carbonate was added until a white suspension
  3. customwas formed
  4. stirringthe reaction mixture was stirred vigorously
  5. filtrationThe reaction mixture was filtered through celite
  6. extractionthe organic material was extracted into 3×100 ml of diethyl ether and 3×100 ml of ethyl acetate
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over sodium sulfate
  9. customthe solvent was evaporated
  10. customThe crude product was recrystallized from hot ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-f6064bc8698041f790a6471ac402bb45
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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