Allyltrimethylsilane → (2S,5R)-5-Allyl-1-methyl-pyrrolidine-2-carboxylic acid phenethyl-amide

HRID 1668422Notes

Reaction equation

HRID 1668422 reaction equation
[CH2:1]([NH:9][C:10]([C@@H:12]1[CH2:16][CH2:15][CH:14](OC)[N:13]1[CH3:19])=[O:11])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:20]([Si](C)(C)C)[CH:21]=[CH2:22]>[Ti](Cl)(Cl)(Cl)Cl.ClCCl>[CH2:1]([NH:9][C:10]([C@@H:12]1[CH2:16][CH2:15][C@H:14]([CH2:22][CH:21]=[CH2:20])[N:13]1[CH3:19])=[O:11])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 69808AllyltrimethylsilaneHCID 66995375(S)-5-Methoxy-1-methyl-pyrrolidine-2-carboxylic acid phenethyl-amide

Product 1

HCID 68811256(2S,5R)-5-Allyl-1-methyl-pyrrolidine-2-carboxylic acid phenethyl-amide

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A dichloromethane (20 mL) solution of 11C methylaminal (7.7 g, 20 mmol) is chilled to −78° C. After 20 minutes, allyltrimethylsilane (6.5 mL, 40 mmol) is added. After 10 more minutes 1 M titanium(IV) chloride (24 mL, 24 mmol) is added slowly by syringe. The reaction is complete after 1 hour. The resulting material is carefully quenched (frothing) with saturated bicarb and extracted with dichlormethane, then washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The product is isolated by flash chromatography (SiO2), and it crystallizes upon standing. LCMS characterization ES+393.1 (m+1).

Workup

  1. waitThe reaction is complete after 1 hour
  2. customThe resulting material is carefully quenched (frothing) with saturated bicarb
  3. extractionextracted with dichlormethane
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product is isolated by flash chromatography (SiO2), and it
  9. customcrystallizes

Sources & evidence

ORD record
ord-8c832a7320bd4faa8bfe16efefa5eb7d
Source dataset
uspto-grants-2011_08
Patent number
US07989441B2

Reaction notes

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