Water → HCID 14552387, compound

HRID 1761682Notes

Reaction equation

HRID 1761682 reaction equation
[NH2:1][C@@H:2]1[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:4][C@H:3]1[C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[CH2:24][CH3:25].O>CN(C=O)C>[CH2:23]([NH:1][C@@H:2]1[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:4][C@H:3]1[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 14552385HCID 14552385, compound

Product 1

HCID 14552387HCID 14552387, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 8-amino-trans-1,4-dioxaspiro[4.5]decane-7-carboxylate (118.0 g, 0.52 mole) was dissolved in DMF (1 l) and potassium carbonate (107 g, 0.77 mole) and propyl bromide (158.4 g, 1.3 mole) were added. The mixture was heated to 50° C. for three hours, then poured into water, and the hydrogen ion concentration was adjusted to pH 10. The product was extracted with methylene chloride, dried and evaporated to give 136 g of a dark orange oil.

Workup

  1. concentrationthe hydrogen ion concentration
  2. extractionThe product was extracted with methylene chloride
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-44b16510fc4a46f58f95c76a3e9cf4a1
Source dataset
uspto-grants-1989_05
Patent number
US04826986

Reaction notes

Loading…