(3SR,4RS)-1-benzyl-3-(4-chloro-phenyl)-4-nitro-pyrrolidine → 1-Benzyl-4-(4-chlorophenyl)pyrrolidin-3-amine

HRID 1951070Notes

Reaction equation

HRID 1951070 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([N+:13]([O-])=O)[CH:10]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.CCOCC.[Ti](Cl)(Cl)(Cl)Cl.[Zn]>[CH2:1]([N:8]1[CH2:9][CH:10]([C:16]2[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=2)[CH:11]([NH2:13])[CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 1

HCID 66940656(3SR,4RS)-1-benzyl-3-(4-chloro-phenyl)-4-nitro-pyrrolidine

Product 1

HCID 669406161-Benzyl-4-(4-chlorophenyl)pyrrolidin-3-amineYield 57%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 24193Titanium TetrachlorideCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
68 °C

Procedure

Titanium (IV) chloride (0.36 g, 1.89 mmol) was added drop wise to a suspension of zinc powder (0.25 g, 3.78 mmol) in THF (3 ml). This solution was heated at 68° C. for one hour, then cooled to RT before rac-(3R,4S)-1-benzyl-3-(4-chloro-phenyl)-4-nitro-pyrrolidine (0.20 g, 0.63 mmol) in THF (2 ml) was added. The reaction mixture was then stirred at reflux over night. The reaction was cooled to RT, diluted with 300 ml of Et2O, washed with an aqueous solution of NaHCO3 and the organic phases were dried over Na2SO4. Flash chromatography (SiO2, CH2Cl2/MeOH, 9:1) yielded 0.10 g (57%) of rac-(3S,4R)-1-benzyl-4-(4-chloro-phenyl)-pyrrolidin-3-ylamine as a light yellow oil.

Workup

  1. additionwas added
  2. temperatureat reflux over night
  3. temperatureThe reaction was cooled to RT
  4. washwashed with an aqueous solution of NaHCO3
  5. dry with materialthe organic phases were dried over Na2SO4

Sources & evidence

ORD record
ord-a927e82ca992440981b7a12e4b4c0619
Source dataset
uspto-grants-2013_03
Patent number
US08404679B2

Reaction notes

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