HCID 59401842, compound → 2-methyl-4-(2-(R)-methyl-[1,3']bipyrrolidinyl-1'-yl)-phenylamine

HRID 415941Notes

Reaction equation

HRID 415941 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH:7]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[C:14]([CH3:21])[CH:13]=2)[CH2:8]1.[H][H]>CO.C(Cl)Cl.[Pd]>[CH3:21][C:14]1[CH:13]=[C:12]([N:9]2[CH2:10][CH2:11][CH:7]([N:3]3[CH2:4][CH2:5][CH2:6][C@H:2]3[CH3:1])[CH2:8]2)[CH:17]=[CH:16][C:15]=1[NH2:18]

Participants

6

Reactant 2

HCID 59401842HCID 59401842, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 594017832-methyl-4-(2-(R)-methyl-[1,3']bipyrrolidinyl-1'-yl)-phenylamineYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(2R)-methyl-1′-(3-methyl-4-nitro-phenyl)[1,3′]bipyrrolidinyl (2 g, 6.9 mmol) in MeOH (15 mL) was de-aerated and nitrogen was introduced. To this solution was added Pd—C (10%, 0.20 g). The nitrogen was replaced with hydrogen and the mixture was stirred under H2 atmosphere at r.t. overnight. TLC (10% MeOH in DCM) and LC/MS showed the reaction was complete. 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, 2.02 g (100% yield).

Workup

  1. additionnitrogen was introduced
  2. washrinsed with methanol
  3. concentrationThe filtrate was concentrated to dryness
  4. customfurther dried under high vacuum

Sources & evidence

ORD record
ord-614e421d883d41b18a092d761499fae7
Source dataset
uspto-grants-2012_01
Patent number
US08088808B2

Reaction notes

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