HCID 538567, compound → HCID 54496779, compound

HRID 2293439Notes

Reaction equation

HRID 2293439 reaction equation
C([Li])CCC.[Cl-].[CH3:7][O:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O=[C:30]1[CH2:35][N:34]2[CH2:36][CH2:37][CH:31]1[CH2:32][CH:33]2[C:38]([O:40][CH3:41])=[O:39]>CCOCC>[CH3:41][O:40][C:38]([CH:33]1[CH2:32][CH:31]2[CH2:37][CH2:36][N:34]1[CH2:35][C:30]2=[CH:7][O:8][CH3:9])=[O:39]

Participants

5

Reactant 3

HCID 538567HCID 538567, compoundHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 178418339Butyllithium

Product 1

HCID 54496779HCID 54496779, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

n-Butyllithium (13,67 ml of a 1.5M solution; 20.5 mmol) was added at 20° to a suspension of methoxymethyltriphenyl phosphonium chloride (7 g, 20.5 mmol) stirred in ether (150 ml) under nitrogen. After 2 h, the mixture was cooled to -35° and a solution of methyl 5-oxoquinuclidine-2-carboxylate (3 g, 16.4 mmol; prepared as described in Zhur. Obshchei. Khim., (1960), 30, 519;see Chem. Abs. (1960), 54: 24723) in ether (20 ml) added. The mixture was allowed to warm to 20° over 1 h and then stirred at this temperature for 16 h. After removing the precipitated triphenylphosphine oxide by filtration, the ether was evaporated off and the resulting oil subjected to chromatography on silica in 3% methanol in dichloromethane to afford the title compound (2.05 g) as a mixture of isomers: m/e 211 (M+); δ(360 MHz, CDCl3) 1.2-2.0 (4H, m, 2×CH2); 2.18-2.34 (1H, m, 4-CH); 2.5-3.4 (5H, m, 2×NCH2 and NCH); 3.50-3.56 (3H, m, OCH3); 3.78-3.82 (3H, m, CO2CH3) and 5.73-5.83 (1H, m, CH).

Workup

  1. temperaturethe mixture was cooled to -35°
  2. temperatureto warm to 20° over 1 h
  3. customAfter removing the precipitated triphenylphosphine oxide
  4. filtrationby filtration
  5. customthe ether was evaporated off

Sources & evidence

ORD record
ord-7d235272ccfc40e78cf48f42936b8530
Source dataset
uspto-grants-1997_11
Patent number
US05686463

Reaction notes

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