Triethylamine → HCID 68008486, compound

HRID 74995Notes

Reaction equation

HRID 74995 reaction equation
[I:1][CH:2]1[CH:8]2[CH2:9][C:5]([CH3:11])([C:6](=[O:10])[NH:7]2)[CH2:4][CH2:3]1.C(N(CC)CC)C.C(=O)(OC(C)(C)C)[O:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[I:1][CH:2]1[CH:8]2[CH2:9][C:5]([CH3:11])([C:6](=[O:10])[N:7]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:20])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 672861264-Iodo-1-methyl-6-azabicyclo[3.2.1]octan-7-one2×

Product 1

HCID 68008486HCID 68008486, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-iodo-1-methyl-6-azabicyclo[3.2.1]octan-7-one, 52c, (9.5 g, 35.8 mmol) in CH2Cl2 (100 mL) was added DMAP (0.2 g, 1.8 mmol), triethylamine (15.0 mL, 107.5 mmol) and tert-butoxycarbonyl tert-butyl carbonate (7.8 g, 35.8 mmol). The reaction was stirred overnight at room temperature. The product was extracted into CH2Cl2 and water. The organic layer was concentrated in vacuo and the residue was purified via silica gel chromatography (4:1 Hexanes:EtOAc), yielding 7.6 g.

Workup

  1. extractionThe product was extracted into CH2Cl2 and water
  2. concentrationThe organic layer was concentrated in vacuo
  3. customthe residue was purified via silica gel chromatography (4:1 Hexanes:EtOAc)
  4. customyielding 7.6 g

Sources & evidence

ORD record
ord-cd8487991f5846e98e15cfc970da5ede
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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