Water → HCID 14552387, compound

HRID 1110777Notes

Reaction equation

HRID 1110777 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-56236e2f62c14fc8a817a919cf645bfe
Source dataset
uspto-grants-1990_12
Patent number
US04977160

Reaction notes

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