Hydrogen Peroxide → HCID 56608405, compound

HRID 2256044Notes

Reaction equation

HRID 2256044 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH:15]=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.[OH-:24].[Na+].OO>O1CCCC1.CO.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][C@@H:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:15]([OH:24])[CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 6331BoraneHCID 14798Sodium HydroxideHCID 11645015HCID 11645015, compound

Product 1

HCID 56608405HCID 56608405, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-benzyloxycarbonyl-4-phenyl-1,2,3,6-tetrahydropyridine (1.0 g) in tetrahydrofuran (20 mL) was cooled to 0° C. and treated with borane:tetrahydrofuran (3.75 mL of 1M solution in tetrahydrofuran). The reaction mixture was stirred for 16 hours at ambient temperature, diluted with methanol (50 mL), and treated with 3N sodium hydroxide (1.25 mL). The resulting reaction mixture was cooled to 0° C. and treated with 30% hydrogen peroxide solution (0.58 mL). After refluxing for 2 hours, the reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The combined organic layers were washed with water and the aqueous layer was extracted with ethyl acetate. Combined organic layers were dried and evaporated to afford the crude product (0.88 g). Chromatography, eluting with hexane:ethyl acetate (3:1) afforded the trans-1-benzyloxycarbonyl-3-hydroxy-4-phenylpiperidine (0.31 g); MS: m/z=312(M+1); NMR: 1.54-1.72 (m, 2), 3.51 (m, 1), 4.02 (m, 1), 4.17 (m, 1), 4.86 (d, 1, J=5), 5.1 (s, 2), 7.17-7.37 (m, 10).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas cooled to 0° C.
  3. temperatureAfter refluxing for 2 hours
  4. temperaturethe reaction mixture was cooled to room temperature
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layers were washed with water
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. customCombined organic layers were dried
  9. customevaporated
  10. customto afford the crude product (0.88 g)
  11. washChromatography, eluting with hexane:ethyl acetate (3:1)

Sources & evidence

ORD record
ord-eff89f55fffd4093a8537e53cc498cba
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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