Hexane → HCID 57650055, compound

HRID 2063457Notes

Reaction equation

HRID 2063457 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[CH:11]=[N:10][N:9]=[C:8]2[C@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:4][CH:3]=1.C([Li])CCC.CCCCCC.[Cl:37]N1C(=O)CCC1=O.C([O-])(O)=O.[Na+]>C1COCC1>[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:11]([Cl:37])=[N:10][N:9]=[C:8]2[C@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 8058HexaneHCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 53486874tert-Butyl (2R)-2-{4-[(4-chlorophenyl)methyl]-4H-1,2,4-triazol-3-yl}pyrrolidine-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 57650055HCID 57650055, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-60 °C

Procedure

To a solution of Boc-protected triazole from Example 3 (4.344 g, 12 mmol) in 20 mL of THF at −60° C. under argon was slowly added a solution of n-butyl lithium (1.6M) in hexane (7.5 mL, 1.2 eq.) and stirred at −60° C. for 30 minutes. To the mixture was added a suspension of N-chlorosuccinimide (4.67 g, 2.9 eq.) in 20 mL of THF and the mixture was kept at −60° C. for 1 hr before warming up to RT overnight. The reaction mixture was treated with sat. aqueous NaHCO3 (30 mL), then extracted with EtOAc (2×40 mL). The organic phase was dried over Na2SO4 and concentrated in vacuo. Flash chromatography purification ((Hex/EtOAc) provided the desired product (1.011 g, 21.2%).

Workup

  1. additionTo the mixture was added
  2. waitthe mixture was kept at −60° C. for 1 hr
  3. temperaturebefore warming up to RT overnight
  4. extractionextracted with EtOAc (2×40 mL)
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customFlash chromatography purification ((Hex/EtOAc)

Sources & evidence

ORD record
ord-44c58635f94f4774968989be674bcc6c
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

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