Pyrrolidine → 4-Pyrrolidin-1-yl-pentanoic acid methyl ester

HRID 1695253Notes

Reaction equation

HRID 1695253 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6]([O:13][CH3:14])(=[O:12])[CH2:7][CH2:8][C:9]([CH3:11])=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.[Cl-].[Na+].O>[CH3:14][O:13][C:6](=[O:12])[CH2:7][CH2:8][CH:9]([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:11]

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 69354Methyl levulinateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 671897684-Pyrrolidin-1-yl-pentanoic acid methyl esterYield 36%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Pyrrolidine (3 mL, 36 mmol, 1.2 eq) was dissolved in DCM (50 mL) and methyl levulinate (4 mL, 30 mmol, 1.0 eq) was added. The solution was stirred at room temperature for 1 hour, then Na(OAc)3BH (7.6 g, 36.0 mmol, 1.2 eq) was added. The mixture was stirred at room temperature for 16 hours, then brine was added, the crude was extracted with DCM and dried. 2.0 g of the title product were obtained (34% yield).

Workup

  1. stirringThe mixture was stirred at room temperature for 16 hours
  2. extractionthe crude was extracted with DCM
  3. customdried

Sources & evidence

ORD record
ord-b4a98ab8a4ad43019dec2a70013669f0
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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