Acetic Acid → Methyl 4-(pyrrolidin-1-ylmethyl)benzoate

HRID 989271Notes

Reaction equation

HRID 989271 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=O)=[CH:6][CH:5]=1.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.C(O)(=O)C.[B-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 15294Methyl 4-FormylbenzoateHCID 31268PyrrolidineHCID 23676153Sodium bis(acetyloxy)boranuidyl acetate

Product 1

HCID 756589Methyl 4-(pyrrolidin-1-ylmethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-formyl-benzoic acid methyl ester (10 g), pyrrolidine (5.6 mL), and acetic acid (3.5 mL) in DCM (200 mL) was treated with sodium triacetoxyborohyride (20.65 g) and stirred at rt for 16 hours. The reaction mixture was then quenched with 3N NaOH (70 mL). The organic layer was dried over sodium sulfate and concentrated to yield the titled compound without purification.

Workup

  1. customThe reaction mixture was then quenched with 3N NaOH (70 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a25891c24d7942d890d9b667f845c4d2
Source dataset
uspto-grants-2003_10
Patent number
US06638967B2

Reaction notes

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