HCID 9884032, compound → HCID 178506684, compound

HRID 1648498Notes

Reaction equation

HRID 1648498 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:8]1[N:12]([CH3:13])[C@H:11]([CH3:14])[C@@H:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:9]1.C([Li:25])CCC>O1CCNC1.C1COCC1>[CH3:13][N:12]1[C@H:11]([CH3:14])[C@@H:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:9][C@@H:8]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Li:25]

Participants

5

Reactant 2

HCID 9884032HCID 9884032, compoundHCID 178418339Butyllithium

Product 1

HCID 178506684HCID 178506684, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 5366831,3-OxazolidineSolvent

Procedure

In a separate flask, the oxazolidine in the form of the mixture of Example 1 (17.43 g, 52.62 mmol, 1 eq) was dissolved in 25 mL of THF under an argon atmosphere. The solution was cooled to -70° C. (internal temperature) and n-C4H9Li (n-BuLi) (21 mL, 52.5 mmol, 1 eq) was added dropwise over 10 min such that the internal temperature did not rise above -50° C. The reaction was brought back to -70° C., and stirred for 2 h.

Workup

  1. additionwas added dropwise over 10 min such that the internal temperature
  2. customdid not rise above -50° C
  3. customwas brought back to -70° C.

Sources & evidence

ORD record
ord-02c7329e20904b40be28239c9dadbfce
Source dataset
uspto-grants-1995_07
Patent number
US05436347

Reaction notes

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