Water → 1-(3,4,5-Trimethoxybenzyl)-3-(phenylmethyl)-3-(2-(t-butyldimethylsilyloxy)ethyl)-2-oxopyrrolidine

HRID 323261Notes

Reaction equation

HRID 323261 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[C:21]([O:25][CH3:26])[C:22]=1[O:23][CH3:24])[CH2:6][N:7]1[CH2:11][CH2:10][CH:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]1=[O:19].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Si:37]([O:44][CH2:45][CH2:46]Br)([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38].O>O1CCCC1.C(OCC)(=O)C.CCCCCC>[CH3:26][O:25][C:21]1[CH:20]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:22]=1[O:23][CH3:24])[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:46][CH2:45][O:44][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[C:8]1=[O:19]

Participants

7

Reactant 4

HCID 962WaterHCID 2733832Lithium HexamethyldisilazideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane2×HCID 184644201-(3,4,5-Trimethoxybenzyl)-3-(phenylmethyl)-2-oxopyrrolidine

Product 1

HCID 184647721-(3,4,5-Trimethoxybenzyl)-3-(phenylmethyl)-3-(2-(t-butyldimethylsilyloxy)ethyl)-2-oxopyrrolidine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
-78 °C

Procedure

Combine 1-(3,4,5-trimethoxybenzyl)-3-(phenylmethyl)-2-oxopyrrolidine (1.0 g, 2.81 mmol) and tetrahydrofuran (10 mL). Cool to −78° C. using a dry-ice/acetone bath. Add a solution of lithium bis(trimethylsilyl)amide (3.09 mL, 1 M in THF, 3.09 mmol). After 30 minutes, add a solution of 2-(t-butyldimethylsilyloxy)ethyl bromide (0.74 g, 3.09 mmol) in tetrahydrofuran (1 mL). After the addition of 2-(t-butyldimethylsilyloxy)ethyl bromide is complete, warm slowly to ambient temperature. After 2 hours, add water and extract three times with ethyl acetate. Dry the combined organic layers over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 1/3 ethyl acetate/hexane to give the title compound: Rf=0.58 (silica gel, 1/3 ethyl acetate/hexane).

Workup

  1. temperaturewarm slowly to ambient temperature
  2. waitAfter 2 hours
  3. extractionextract three times with ethyl acetate
  4. dry with materialDry the combined organic layers over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customto obtain a residue

Sources & evidence

ORD record
ord-604e55be661641bf90b75a688716bbff
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

Loading…