Triethylamine → HCID 68008486, compound

HRID 527023Notes

Reaction equation

HRID 527023 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-e15b95ccff7c49b3a72ee7af327b093f
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Reaction notes

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