Water → HCID 19839071, compound

HRID 1639402Notes

Reaction equation

HRID 1639402 reaction equation
[N+]([O-])([O-])=O.[NH4+].[Ce+4].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.COC1C=CC(C[N:30]2[C:35](=[O:36])[CH:34]3[CH2:37][C:32]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)([CH2:33]3)[C:31]2=[O:44])=CC=1.O>C(#N)C>[C:38]1([C:32]23[CH2:33][CH:34]([CH2:37]2)[C:35](=[O:36])[NH:30][C:31]3=[O:44])[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9869224Ammonium cerium (IV) nitrateHCID 19839083HCID 19839083, compound

Product 1

HCID 19839071HCID 19839071, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 344 g of cerium(IV) ammonium nitrate in 1.1 1 of acetonitrile is added dropwise to a stirred solution of 53 g of 3-(4-methoxybenzyl)-1-phenyl-3-azabicyclo[3.1.1]heptane-2,4-dione in 560 ml of acetonitrile at room temperature. After 1 hour, 515 ml of water are added and the mixture is stirred for 2 hours. It is concentrated to half the volume by distilling off the acetonitrile and is then diluted with 1 1 of water. The product which has precipitated is filtered off with suction, washed with water and dried in vacuo. The brown-yellowish crystalline substance is taken up in 800 ml of methylene chloride, 11 ml of n-propylamine are added and the mixture is left to stand overnight. The black solution is concentrated and 80 ml of methylene chloridediethyl ether (1:1) are added to the brown crystalline mass, and the crystals are filtered off with suction and dried under a high vacuum. The title compound is obtained as white crystals of m.p. 217-218° C.

Workup

  1. concentrationIt is concentrated to half the volume
  2. distillationby distilling off the acetonitrile
  3. additionis then diluted with 1 1 of water
  4. customThe product which has precipitated
  5. filtrationis filtered off with suction
  6. washwashed with water
  7. customdried in vacuo
  8. addition11 ml of n-propylamine are added
  9. waitthe mixture is left
  10. waitto stand overnight
  11. concentrationThe black solution is concentrated
  12. addition80 ml of methylene chloridediethyl ether (1:1) are added to the brown crystalline mass
  13. filtrationthe crystals are filtered off with suction
  14. customdried under a high vacuum

Sources & evidence

ORD record
ord-dbb66c7efd3b428c91665401d5a44a1f
Source dataset
uspto-grants-1989_11
Patent number
US04883877

Reaction notes

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