Triethylamine → 2-(4-Benzyloxyphenyl)-8-(tert-butyldimethylsilanyloxymethyl)-1-ethylindolizine

HRID 1422110Notes

Reaction equation

HRID 1422110 reaction equation
[CH2:1]([C:3]1[C:4]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:16][CH:15]=2)=[CH:5][N:6]2[C:11]=1[C:10]([CH2:12][OH:13])=[CH:9][CH:8]=[CH:7]2)[CH3:2].C(N(CC)CC)C.[Si:35](Cl)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36]>ClCCl>[CH2:21]([O:20][C:17]1[CH:18]=[CH:19][C:14]([C:4]2[C:3]([CH2:1][CH3:2])=[C:11]3[N:6]([CH:5]=2)[CH:7]=[CH:8][CH:9]=[C:10]3[CH2:12][O:13][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])=[CH:15][CH:16]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 187069521-Ethyl-2-(4-benzyloxyphenyl)-8-hydroxymethylindolizine

Product 1

HCID 187069342-(4-Benzyloxyphenyl)-8-(tert-butyldimethylsilanyloxymethyl)-1-ethylindolizineYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Ethyl-2-(4-benzyloxyphenyl)-8-hydroxymethylindolizine (21.3 g, 60 mmol), triethylamine (7.88 g, 78 mmol) and tert-butyldimethylsilylchloride (17.8 g, 118 mmol) was dissolved in 200 ml of dry dichloromethane, and the mixture was stirred for 2 days. The solvent was evaporated and the crude product was purified by column chromatography over silica gel 60, using diethyl ether as the eluent. Fractions containing the product were combined and the solvent was evaporated. The product was crystallised from diethyl ether and petroleum ether to afford 25.5 g (90%) of 2-(4-benzyloxyphenyl)-8-(tert-butyldimethylsilanyloxymethyl)-1-ethylindolizine as yellow crystals. M.p. 79-81° C. 1H--NMR (CDCl3, 200 MHz) δ: 0.01 (s, 6 H); 0.83 (s, 9 H); 1.02 (t, 3 H); 2.74 (q, 2 H); 4.92 (s, 2 H); 4.96 (s, 2 H); 6.25 (dd, 1 H); 6.61 (d, 1 H); 6.89 (d, 2 H); 7.11 (s, 1 H); 7.17-7.37 (m, 7 H); 7.59 (d, 1 H).

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was purified by column chromatography over silica gel 60
  3. additionFractions containing the product
  4. customthe solvent was evaporated
  5. customThe product was crystallised from diethyl ether and petroleum ether

Sources & evidence

ORD record
ord-c1427e6581cc4000b3880c5b5deefca9
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

Loading…