Sodium Hydroxide → HCID 21105647, compound

HRID 2426715Notes

Reaction equation

HRID 2426715 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][CH:12]([NH:15][C:16](=[O:22])OC(C)(C)C)[CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].Cl[CH2:32][CH2:33][CH2:34]C(Cl)=O.[OH-].[Na+]>C(#N)C.O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:14][CH2:13][C@@H:12]([N:15]3[CH2:34][CH2:33][CH2:32][C:16]3=[O:22])[CH2:11]2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 24243Trisodium PhosphateHCID 783704-Chlorobutyryl chlorideHCID 21918751HCID 21918751, compound

Product 1

HCID 21105647HCID 21105647, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

tert-Butyl [1-(4-Nitrophenyl)pyrrolidin-3-yl]carbamate was treated by method G. The crude product (1.4 g) was dissolved in acetonitrile (20 ml) and mixed with trisodium phosphate (0.67 g) and 4-chlorobutyryl chloride (1.1 g). After 2 hours, sodium hydroxide (0.6 g) in water (10 ml) was added and the mixture was vigorously stirred. After 12 hours, the same amount of sodium hydroxide solution was again added, and the mixture was stirred for a further 24 hours. The concentrated reaction solution was partitioned between water and ethyl acetate, and the organic phase was dried and concentrated. The residue was hydrogenated by method B. This resulted in the product with the molecular weight of 245.33 (C14H19N3O); MS (ESI): 246 (M+H+).

Workup

  1. waitAfter 12 hours
  2. stirringthe mixture was stirred for a further 24 hours
  3. customThe concentrated reaction solution
  4. customwas partitioned between water and ethyl acetate
  5. customthe organic phase was dried
  6. concentrationconcentrated
  7. customThis resulted in the product with the molecular weight of 245.33 (C14H19N3O)

Sources & evidence

ORD record
ord-e6814c8731c947aa84e16b7f5a0364c6
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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