Sodium hydride → HCID 20043203, compound

HRID 1762295Notes

Reaction equation

HRID 1762295 reaction equation
[H-].[Na+].[C:3]12([OH:13])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.[C:14]([N:18]1[CH2:22][CH2:21][O:20][P:19]1Cl)([CH3:17])([CH3:16])[CH3:15]>C1COCC1>[C:3]12([O:13][P:19]3[N:18]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:22][CH2:21][O:20]3)[CH2:10][CH:9]3[CH2:8][CH:7]([CH2:6][CH:5]([CH2:11]3)[CH2:4]1)[CH2:12]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 641521-AdamantanolHCID 142281093-tert-Butyl-2-chloro-1,3,2-oxazaphospholidine

Product 1

HCID 20043203HCID 20043203, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

A 500 ml, three neck flask equipped with a thermometer, an additional funnel and a condenser topped with a nitrogen sweep is charged with 2.62 g (0.06 mol) of sodium hydride. The sodium hydride is washed with two 20 ml portions of hexane and finally suspended in 30 ml of tetrahydrofuran. To the resultant suspension is added dropwise a solution of 9.12 g (0.06 mol) of 1-adamantanol in 75 ml of THF at such rate to keep the reaction temperature between 20°-30° C. The resulting yellow solution is warmed to approximately 40° C. for 1 hour and then cooled in an ice bath. A solution of 10.9 g (0.06 mol) of 3-tert-butyl-2-chloro-1,3,2-oxazaphospholidine in 75 ml of THF is added and stirring continued for 16 hours at room temperature. The resulting cloudy mixture is filtered and the solvent evaporated under reduced pressure. The residue is treated with 200 ml of toluene and the resultant suspension is filtered. The filtrate is concentrated in vacuo to yield a thick syrup. Triturating with methanol gives 6.0 g (33.6%) of a white solid: m.p. 48°-50° C.

Workup

  1. customA 500 ml, three neck flask equipped with a thermometer, an additional funnel and a condenser
  2. washThe sodium hydride is washed with two 20 ml portions of hexane
  3. custombetween 20°-30° C
  4. temperaturecooled in an ice bath
  5. filtrationThe resulting cloudy mixture is filtered
  6. customthe solvent evaporated under reduced pressure
  7. additionThe residue is treated with 200 ml of toluene
  8. filtrationthe resultant suspension is filtered
  9. concentrationThe filtrate is concentrated in vacuo
  10. customto yield a thick syrup
  11. customTriturating with methanol

Sources & evidence

ORD record
ord-9f0c745c2d114de9b458d99e15a2391c
Source dataset
uspto-grants-1989_05
Patent number
US04831178

Reaction notes

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