Tempo → HCID 91277295, compound

HRID 712796Notes

Reaction equation

HRID 712796 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:9][CH:8]2[CH:6]([CH2:7]2)[CH2:5][N:4]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].CC1(C)N([O])C(C)(C)CCC1>C(Cl)Cl>[CH:2]([CH:3]1[CH2:9][CH:8]2[CH:6]([CH2:7]2)[CH2:5][N:4]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:1]

Participants

4

Reactant 2

HCID 2724126TempoHCID 75302735HCID 75302735, compound

Product 1

HCID 91277295HCID 91277295, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 4-(hydroxymethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate (D15) (820 mg, 3.6 mmol) and TEMPO (112.7 mg, 0.72 mmol) in DCM (8 ml), BAlB (1.27 g, 3.96 mmol) was added and the resulting mixture was stirred at RT 4 hrs. The reaction mixture was diluted with DCM (35 ml), washed with Na2S2O3 sat sol (35 ml) and extracted with DCM (2×35 ml). The combined organic extracts were washed with NaHCO3 sat sol (35 ml) and brine (35 ml), dried and evaporated under reduce pressure. The remaining residue was loaded on SPE-Si (25 g) cartridge and eluted with a mixture cHex/EtOAC from 95/05 to 80/20. Collected fractions after solvent evaporation afforded the title compound (D16) (0.62 g).

Workup

  1. washwashed with Na2S2O3
  2. extractionextracted with DCM (2×35 ml)
  3. washThe combined organic extracts were washed with NaHCO3
  4. customdried
  5. customevaporated
  6. washeluted with a mixture cHex/EtOAC from 95/05 to 80/20
  7. customCollected fractions after solvent evaporation

Sources & evidence

ORD record
ord-2466789249b44604bf21ca60bd1673b1
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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