Citric Acid → HCID 178451936, compound

HRID 29073Notes

Reaction equation

HRID 29073 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]#[N:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:15]=[N+:16]=[N-:17].[Na+].[Cl-].[NH4+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[NH:17][N:16]=[N:15][N:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 6951263tert-butyl (2S)-2-cyanopyrrolidine-1-carboxylate

Product 1

HCID 178451936HCID 178451936, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
93 °C

Procedure

To a solution of (S)-2-Cyano-pyrrolidine-1-carboxylic acid tert-butyl ester (500 mg, 2.55 mmol) in N,N-dimethyl-formamide (20 mL) is added sodium azide (174 mg, 2.68 mmol) and ammonium chloride (150 mg, 2.81 mmol). The solution is stirred at 93° C. over night. The solution is poured into 5% citric acid solution with ice, and the mixture is extracted with EtOAc. The organic extract is washed with brine, dried and concentrated under vacuum. The crude oil is used directly in the next step without further purification. M+H+=240.

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. extractionThe organic extract
  3. washis washed with brine
  4. customdried
  5. concentrationconcentrated under vacuum
  6. customThe crude oil is used directly in the next step without further purification

Sources & evidence

ORD record
ord-a8750b999fa54cdb82a4adfeb92d81df
Source dataset
uspto-grants-2008_09
Patent number
US07419975B2

Reaction notes

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