Sodium Carbonate → HCID 67853110, compound

HRID 1728419Notes

Reaction equation

HRID 1728419 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:12][N:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH:6]2[CH2:5][CH2:4]1.[CH2:13]([O:20][C:21](Cl)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O.O.CC(C)=O>[CH2:13]([O:20][C:21]([N:10]1[CH2:9][CH2:8][N:7]2[CH2:12][CH:3]([CH2:2][OH:1])[CH2:4][CH2:5][CH:6]2[CH2:11]1)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 12985539(Octahydro-1H-pyrido[1,2-A]pyrazin-7-YL)methanol

Product 1

HCID 67853110HCID 67853110, compoundYield 30.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a solution of the title product of Example 6 (640 mg, 3.76 mmol) in acetone/water (6.3 ml and 2.2 ml, respectively), a solution of benzylchloroformate (0.61 ml, 729 mg, 4.27 mmol) in acetone (2.0 ml) was added dropwise over several minutes while maintaining the pH of the mixture at 9.5 by intermittent dropwise addition of saturated aqueous sodium carbonate. After completing the addition, the reaction was stirred for 5 minutes at ambient temperature. The acetone solvent was removed in vacuo, ethyl acetate (60 ml) and water (30 ml) were added, and the pH of the well-stirred mixture was adjusted to 9.5 (sodium carbonate). The separated organic phase was dried (anhydrous sodium sulfate) and concentrated in vacuo to an oil (940 mg). Flash chromatography of the entire sample [10 g, silica gel, 32-63 mesh, eluting initially with ethyl acetate (100 mg), followed by ethyl acetate/methanol (100 ml, 97:3 in volume) and finally ethyl acetate/methanol (200 ml, 90:10 in volume)] afforded the present title compound as a colorless oil, 350 mg (30.6% yield). TLC Rf (ethyl acetate/methanol/concentrated aqueous ammonia=9:2:0.2 in volume): 0.63.

Workup

  1. temperaturewhile maintaining the pH of the mixture at 9.5
  2. additionthe addition
  3. customThe acetone solvent was removed in vacuo, ethyl acetate (60 ml) and water (30 ml)
  4. additionwere added
  5. dry with materialThe separated organic phase was dried (anhydrous sodium sulfate)
  6. concentrationconcentrated in vacuo to an oil (940 mg)
  7. washFlash chromatography of the entire sample [10 g, silica gel, 32-63 mesh, eluting initially with ethyl acetate (100 mg)

Sources & evidence

ORD record
ord-2cd34027ac344e8595ee9debccdf6c16
Source dataset
uspto-grants-1994_07
Patent number
US05326874

Reaction notes

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