Acetic Acid → 1-Benzyl-4-(benzylamino)-pyrrolidine-2-carboxylic acid methyl ester

HRID 490580Notes

Reaction equation

HRID 490580 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][C:8](=O)[CH2:7][N:6]1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:4].[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([NH:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:7][N:6]1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 67548133Benzyl-4-oxo-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 675488361-Benzyl-4-(benzylamino)-pyrrolidine-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-Benzyl-4-oxo-pyrrolidine-2-carboxylic acid methyl ester and a corresponding benzylamine are dissolved in DCM, acetic acid and NaBH(OAc)3 is then added. After stirred for about 3 hours the reaction mixture is diluted with DCM, washed, dried and concentrated. The residue is purified to afford 1-benzyl-4-(benzylamino)-pyrrolidine-2-carboxylic acid methyl ester (26).

Workup

  1. washwashed
  2. customdried
  3. concentrationconcentrated
  4. customThe residue is purified

Sources & evidence

ORD record
ord-70c3a89c2bae48c99a026ba484baebd5
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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