4-Chloro-2-nitrobenzaldehyde → HCID 66758130, compound

HRID 557016Notes

Reaction equation

HRID 557016 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[C:17]([N+:23]([O-:25])=[O:24])[CH:16]=1.[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][CH2:19][C:18]2[CH:21]=[CH:22][C:15]([Cl:14])=[CH:16][C:17]=2[N+:23]([O-:25])=[O:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 796744-Chloro-2-nitrobenzaldehydeHCID 27563701-Boc-3-aminopyrrolidineHCID 4311764Sodium borohydride

Product 1

HCID 66758130HCID 66758130, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-Amino-pyrrolidine-1-carboxylic acid tert-butyl ester (2 g, 10.7 mmol) in methanol (20 mL) was added 4-Chloro-2-nitro-benzaldehyde (1.98 g, 10.7 mmol). The resultant solution was heated at 60° C. overnight. The reaction mixture was cooled to 0° C. and to it was added NaBH4 (629 mg, 10 mmol). After 1 h, the reaction solution was quenched with saturated NaHCO3 solution and extracted with ethyl acetate. The organic extract was dried over MgSO4, filtered and concentrated to provide the crude product as an oil. The crude product was used in the subsequent reaction without further purification. LCMS (retention time=1.28, ES+; 356)

Workup

  1. customthe reaction solution was quenched with saturated NaHCO3 solution
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cf2f0dd3fd274ea9afa23e2750aa125c
Source dataset
uspto-grants-2011_11
Patent number
US08058287B2

Reaction notes

Loading…