Water → 3-Aminopropyl(1-hydroxycyclobutyl)phosphinic acid

HRID 1612698Notes

Reaction equation

HRID 1612698 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][P:5]([OH:7])[OH:6].[C:8]1(=[O:12])[CH2:11][CH2:10][CH2:9]1.O>C[Si](C)(C)N[Si](C)(C)C.Cl>[NH2:1][CH2:2][CH2:3][CH2:4][P:5]([C:8]1([OH:12])[CH2:11][CH2:10][CH2:9]1)(=[O:7])[OH:6]

Participants

6

Reactant 3

HCID 962WaterHCID 14496CyclobutanoneHCID 99892683-Amino-propanephosphonous

Product 1

HCID 99423723-Aminopropyl(1-hydroxycyclobutyl)phosphinic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 13838HexamethyldisilazaneSolvent

Procedure

A suspension of 2.46 g of 3-aminopropylphosphonous acid in 20 ml of hexamethyldisilazane is heated to reflux under an inert gas for 24 hours. The resulting clear solution is cooled to 15° and 2.0 ml of cyclobutanone are added. An exothermic reaction ensues. The reaction mixture is stirred until the temperature drops to room temperature (approximately 1 hour). Water is added and the volatile materials are removed in vacuo to yield a semi-solid. This is dissolved in 2.0M aqueous hydrochloride acid and washed with 2×100 ml of dichloromethane. The aqueous layer is evaporated in vacuo to afford a solid which is passed through a DOWEX® 50 W×8 (14-40 mesh) ion-exchange column to give 3-aminopropyl(1-hydroxycyclobutyl)phosphinic acid, m.p. 174°-175° (dec).

Workup

  1. temperatureis heated
  2. temperatureto reflux under an inert gas for 24 hours
  3. temperatureThe resulting clear solution is cooled to 15°
  4. customAn exothermic reaction
  5. customdrops to room temperature
  6. custom(approximately 1 hour)
  7. customthe volatile materials are removed in vacuo
  8. customto yield a semi-solid
  9. washwashed with 2×100 ml of dichloromethane
  10. customThe aqueous layer is evaporated in vacuo
  11. customto afford a solid which

Sources & evidence

ORD record
ord-8a1853099bfc484d9ea206eb4acbc29e
Source dataset
uspto-grants-1993_03
Patent number
US05190933

Reaction notes

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