Benzylamine → (R)-1-benzyl-2-methylpyrrolidine

HRID 1157102Notes

Reaction equation

HRID 1157102 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C@@H:9](OS(C)(=O)=O)[CH3:10])(=O)=O.[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[Na+]>C(OCC)(=O)C>[CH2:16]([N:23]1[CH2:10][CH2:9][CH2:8][C@H:7]1[CH3:6])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 86616918HCID 86616918, compound

Product 1

HCID 58620094(R)-1-benzyl-2-methylpyrrolidineYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

First, 2.49 g (9.6 mmol) of (S)-1,4-bis(methanesulfonyloxy)pentane produced in Example 5 and 5.13 g (47.9 mmol) of benzylamine were stirred at 70° C. for three hours. Subsequently, 30 mL of ethyl acetate and 4.0 g of a 20 weight percent aqueous solution of sodium hydroxide were added to the mixture to perform an extraction. The organic layer was concentrated under a reduced pressure to obtain a yellow oily substance. This product was purified by silica gel column chromatography. Thus, (R)-1-benzyl-2-methylpyrrolidine was obtained as a light yellow oily substance (1.83 g, yield: 100%).

Workup

  1. extractionan extraction
  2. concentrationThe organic layer was concentrated under a reduced pressure
  3. customto obtain a yellow oily substance
  4. customThis product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-edceab3b36fa4b8e8de15299a09362c6
Source dataset
uspto-grants-2010_10
Patent number
US07807426B2

Reaction notes

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