Methanol → HCID 68089279, compound

HRID 1918232Notes

Reaction equation

HRID 1918232 reaction equation
C[O:2][C:3]([CH:5]1[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)([CH3:10])[CH2:8][N:7]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:6]1)=[O:4].[Li+].[OH-].CO>C1COCC1>[CH2:18]([N:7]1[CH2:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)([CH3:10])[CH:5]([C:3]([OH:4])=[O:2])[CH2:6]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 68089112HCID 68089112, compound

Product 1

HCID 68089279HCID 68089279, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 9.56 g (27.8 mmol) rac-(3S,4R)-1-Benzyl-4-(4-chloro-phenyl)-4-methyl-pyrrolidine-3-carboxylic acid methyl ester and 3.5 g (83.4 mmol) LiOH.H20 in 50 mL THF/50 mL water and 5 mL methanol was heated to reflux and stirred over night. The organic solvents were removed under vacuum and the aqueous phase was adjusted to pH=4-5 with 1N HCl aq. Water was decanted off the residue and THF was added. The mixture was diluted with ethyl acetate and washed with brine. The aqueous layer was back-extracted with ethyl acetate/THF (1:1) and the organic layers were evaporated to yield 8.9 g (97%) of the title compounds as off-white solid. MS m/e: 328.3 [M−H].

Workup

  1. temperatureto reflux
  2. customThe organic solvents were removed under vacuum
  3. customwas decanted off the residue and THF
  4. additionwas added
  5. additionThe mixture was diluted with ethyl acetate
  6. washwashed with brine
  7. extractionThe aqueous layer was back-extracted with ethyl acetate/THF (1:1)
  8. customthe organic layers were evaporated

Sources & evidence

ORD record
ord-7f5be4d6a2334df9b3086a38838d28ed
Source dataset
uspto-grants-2013_12
Patent number
US08618303B2

Reaction notes

Loading…