Acetic Acid → HCID 14041199, compound

HRID 490571Notes

Reaction equation

HRID 490571 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([N:10]=[N+:11]=[N-:12])[CH2:7][N:6]1[C:13](OC(C)(C)C)=O)=[O:4].[C:20](O)(=O)[CH3:21].[BH-](O[C:34]([CH3:36])=O)(OC(C)=O)OC(C)=O.[Na+].[C:38](O)([C:40](F)(F)F)=O.C(Cl)Cl>C(Cl)Cl>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([N:10]=[N+:11]=[N-:12])[CH2:7][N:6]1[CH2:13][C:21]1[CH:20]=[CH:36][CH:34]=[CH:40][CH:38]=1)=[O:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 147726831-Tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylateHCID 21863450Trifluoroacetic acid methylene chloride

Product 1

HCID 14041199HCID 14041199, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-azido-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester in CF3COOH/CH2Cl2 is stirred overnight at room temperature. To a solution of the obtained product in DCM is added a corresponding unsubstituted or halogen-substituted benzaldehyde, acetic acid and NaBH(OAc)3. After stirred overnight, the reaction mixture is purified to afford the corresponding product 4-azido-1-benzyl-pyrrolidine-2-carboxylic acid methyl ester (9).

Workup

  1. stirringAfter stirred overnight
  2. customthe reaction mixture is purified

Sources & evidence

ORD record
ord-f3093227f1c54790a3ff1a2f3b60669c
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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