HCID 72270949, compound → HCID 75302735, compound

HRID 712795Notes

Reaction equation

HRID 712795 reaction equation
[Si]([O:18][CH2:19][CH:20]1[CH2:26][CH:25]2[CH:23]([CH2:24]2)[CH2:22][N:21]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[OH:18][CH2:19][CH:20]1[CH2:26][CH:25]2[CH:23]([CH2:24]2)[CH2:22][N:21]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]

Participants

4

Reactant 1

HCID 72270949HCID 72270949, compound

Product 1

HCID 75302735HCID 75302735, compoundYield 90.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

To a solution of tert-butyl 4-(((tert-butyldiphenylsilyl)oxy)methyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate (D14) (2.10 g, 4.5 mmol) in THF (80 ml), TBAF 1M sol. in THF (9.01 ml) was added and the reaction mixture was stirred at RT for 18 hrs. Solvents were evaporated in vacuo and the resulting residue was purified on SPE-Si (5 g) cartridge eluting with a mixture cHex/EtOAc from 90/10 to 40/60. Collected fractions after solvent evaporation afforded the title compound (D15) (0.93 g).

Workup

  1. customSolvents were evaporated in vacuo
  2. customthe resulting residue was purified on SPE-Si (5 g) cartridge
  3. washeluting with a mixture cHex/EtOAc from 90/10 to 40/60
  4. customCollected fractions after solvent evaporation

Sources & evidence

ORD record
ord-e1d94b6908ad48a3bfea79813a4eccc7
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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