HCID 59401909, compound → HCID 59401910, compound

HRID 1516541Notes

Reaction equation

HRID 1516541 reaction equation
[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C@H:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]([CH3:22])[CH:14]=2)[CH2:9]1>CO.C(Cl)Cl.[Pd]>[CH3:22][C:15]1[CH:14]=[C:13]([N:10]2[CH2:11][CH2:12][C@H:8]([CH2:7][N:3]3[CH2:4][CH2:5][CH2:6][C@@H:2]3[CH3:1])[CH2:9]2)[CH:18]=[CH:17][C:16]=1[NH2:19]

Participants

5

Reactant 1

HCID 59401909HCID 59401909, compound

Product 1

HCID 59401910HCID 59401910, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of (2S,3R)-2-methyl-1-[1-(3-methyl-4-nitro-phenyl)-pyrrolidin-3-yl-methyl]-pyrrolidine (0.3 g, 1 mmol) in MeOH (15 mL) was deaerated and nitrogen was introduced. To this solution was added Pd—C (10%, 30 mg). This mixture was stirred under H2 atmosphere at r.t. overnight. TLC (10% MeOH in DCM) and LC/MS showed the reaction was complete, product peak was observed at t=1.458 min, m/z: 274 (M). The mixture was passed through a Celite pad, rinsed with methanol. The filtrate was concentrated to dryness, and further dried under high vacuum to yield the title compound as a reddish brown liquid after drying under high vacuum.

Workup

  1. additionnitrogen was introduced
  2. customwas observed at t=1.458 min, m/z
  3. washrinsed with methanol
  4. concentrationThe filtrate was concentrated to dryness
  5. customfurther dried under high vacuum

Sources & evidence

ORD record
ord-a2582412dfbe4b03b023683e30529f70
Source dataset
uspto-grants-2012_07
Patent number
US08227504B2

Reaction notes

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