Triethylamine → HCID 58348963, compound

HRID 536592Notes

Reaction equation

HRID 536592 reaction equation
[CH2:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:18](OC([O-])=O)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>ClCCl>[CH2:4]1[C:5]2([CH2:10][CH2:9][N:8]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:7][CH2:6]2)[CH2:1][CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4371528-Azaspiro(4.5)decaneHCID 22064466Tert-butyldicarbonate

Product 1

HCID 58348963HCID 58348963, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 8-azaspiro[4.5]decane (which has been described in WO 9800404 A1 6.2 g, 44.5 mmol) in dichloromethane (130 ml), which was cooled to 0° C., triethylamine (7.5 ml, 53.4 mmol) was added then a solution of tert-butyl dicarbonate (10.68 g, 48.9 mmol) in dichloromethane (50 ml) was added in 20 minutes. The clear solution was maintained under stirring at room temperature for 18 hours, then dichloromethane (50 ml) was added and the organic solution was washed with water (2×20 ml), HCl 0.1N (20 ml) then water (2×20 ml). The organic solvent was anhydrified (Na2SO4) and evaporated to give a crude that was purified on silica gel column (Hexane/AcOEt 95/5) to give 6 g of the title compound (light yellow solid).

Workup

  1. temperatureThe clear solution was maintained
  2. washthe organic solution was washed with water (2×20 ml), HCl 0.1N (20 ml)
  3. customevaporated
  4. customto give a crude that
  5. customwas purified on silica gel column (Hexane/AcOEt 95/5)

Sources & evidence

ORD record
ord-f9cb358b01454eddb168284c6e3cec27
Source dataset
uspto-grants-2014_10
Patent number
US08859608B2

Reaction notes

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