Morpholine → 3-(3-Chloro-5-fluorophenyl)-1-ethylpyrrolidin-3-ol

HRID 1931853Notes

Reaction equation

HRID 1931853 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)([OH:13])[CH2:9]1)[C:2]1C=CC=CC=1.N1CCOCC1>CN(C)C=O>[Cl:21][C:16]1[CH:15]=[C:14]([C:10]2([OH:13])[CH2:11][CH2:12][N:8]([CH2:1][CH3:2])[CH2:9]2)[CH:19]=[C:18]([F:20])[CH:17]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 685158581-Benzyl-3-(3-chloro-5-fluorophenyl)pyrrolidin-3-ol

Product 1

HCID 251457773-(3-Chloro-5-fluorophenyl)-1-ethylpyrrolidin-3-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Preparation according to Example 34: (+)-1-benzyl-3-(3-chloro-5-fluorophenyl)-pyrrolidin-3-ol (0.1 g, 0.33 mmol) iodoethane (1 mL, 12.37 mmol), dimethyl formamid (2 mL), morpholine (2 mL). Purification by flash chromatography on silica gel (ethyl acetate/methanol, 1:0 to 1:1). Yield: 0.05 g. [α]D=+16.7° (methanol). The amine was converted to the oxalic acid salt and recrystallized from ethanol/diisopropyl ether: M.p. 113-114° C.; MS m/z (relative intensity, 70 eV) 243 (M+, 6), 157 (7), 129 (11), 72 (33), 71 (bp).

Workup

  1. customPreparation
  2. customPurification by flash chromatography on silica gel (ethyl acetate/methanol, 1:0 to 1:1)
  3. customrecrystallized from ethanol/diisopropyl ether

Sources & evidence

ORD record
ord-0a7bd4dc617047c681797e5e313adba3
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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