Ammonia → HCID 86724981, compound

HRID 1847056Notes

Reaction equation

HRID 1847056 reaction equation
[Na].N.[Si:3]([O:10][CH2:11][C@H:12]1[CH2:16][N:15]([C@@H](C2C=CC=CC=2)C)[C:14](=[O:25])[CH2:13]1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[Cl-].[NH4+]>O1CCCC1.C(O)(C)(C)C>[Si:3]([O:10][CH2:11][C@H:12]1[CH2:16][NH:15][C:14](=[O:25])[CH2:13]1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 12076457(4R)-4-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-1-[(1R)-1-phenylethyl]-2-pyrrolidinone

Product 1

HCID 86724981HCID 86724981, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen gas atmosphere, metallic sodium (920 mg, 40.0 mmol) was added to liquid ammonia (about 30 ml) at −78° C. over a period of 5 minutes, and the mixture was further stirred at the same temperature for 15 minutes. To the reaction solution, a solution of (4R)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1-[(1R)-1-phenylethyl]pyrrolidin-2-one (Heterocycles, 2003, vol. 60, No. 11, pages 2485-2498, or synthesized with reference to JP09136886; 3.34 g, 10.0 mmol) in tetrahydrofuran (10 ml)/tert-butyl alcohol (1 ml) was added over a period of 5 minutes and the mixture was stirred for about 1 hour. Ammonium chloride (3.21 g) was added thereto, and ammonia was evaporated by gradually raising the temperature to room temperature when the color of the reaction solution changed from dark blue to colorless. Water was added to dissolve the insoluble material and the resultant was extracted with a mixed solution of chloroform-methanol (9:1). The organic layer was dried over anhydrous sodium sulfate, the drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to yield 2.29 g (100%) of the title compound in the form of a colorless oily product.

Workup

  1. custom11, pages 2485-2498, or synthesized with reference to JP09136886
  2. stirringthe mixture was stirred for about 1 hour
  3. customammonia was evaporated
  4. additionWater was added
  5. dissolutionto dissolve the insoluble material
  6. extractionthe resultant was extracted with a mixed solution of chloroform-methanol (9:1)
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customthe drying agent was removed by filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c34a602ff1704a3b9dd3e851cca56093
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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