Ethylamine → N-ethyl-1,4-dioxaspiro[4.5]decan-8-amine

HRID 2175543Notes

Reaction equation

HRID 2175543 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH2:12]([NH2:14])[CH3:13].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(#N)C>[CH2:12]([NH:14][CH:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)[CH3:13]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 15342646N-ethyl-1,4-dioxaspiro[4.5]decan-8-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,4-dioxaspiro[4.5]decan-8-one (2 g, 12.8 mmol), and ethylamine (6.4 mL, 12.8 mmol), and sodium triacetoxyborohydride (8 g, 38 mmol) were taken in acetonitrile and stirred for 18 h at room temperature. The mixture concentrated under vacuum and the residue basified with NaHCO3, saturated with solid NaCl and extracted with EtOAc/iPrOH (4:1) four times. Organic layer separated, dried over Na2SO4 and evaporated to give the title compound.

Workup

  1. concentrationThe mixture concentrated under vacuum
  2. extractionextracted with EtOAc/iPrOH (4:1) four times
  3. customOrganic layer separated
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-5bec336cc4c64903a80ce942a13ab777
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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