Hydrogen Peroxide → HCID 53840815, compound

HRID 1086262Notes

Reaction equation

HRID 1086262 reaction equation
[C:1]([O:9][CH:10]([CH2:57][CH:58]=[CH2:59])[CH:11]1[CH:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:15]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:14]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:13]([CH2:41][O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[N:12]1[CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:60].[Na+].OO.O>O1CCCC1>[C:1]([O:9][CH:10]([CH:11]1[CH:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:15]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:14]([O:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:13]([CH2:41][O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[N:12]1[CH2:50][C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)[CH2:57][CH2:58][CH2:59][OH:60])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 53884909HCID 53884909, compound

Product 1

HCID 53840815HCID 53840815, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Compound (XIV) (1.80 g; 2.29 mmoles) in tetrahydrofuran (25 mL), cooled at 0° C., was added a 1.0M solution of borane-dimethylsulfide complex in tetrahydrofuran (1.5 mL). The reaction was warmed to room temperature and kept for 20 hours. After cooling to 0° C., 3N NaOH solution (15 mL) and 30W% hydrogen peroxide (0.5 mL) were added, and the suspension was heated under reflux for 1 hour. Upon cooling to room temperature, the suspension was mixed with water (10 mL) and extracted with ether (2×40 mL). The combined organic solution was washed with saturated sodium chloride solution, dried over magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the crude residual oil was purified via flash chromatography (silica gel; 1:2 ethyl acetate:hexane) to yield the primary alcohol, 1-[3,4,5-tris(phenylmethoxy)-6[(phenylmethoxy) methyl]-1-(phenylmethyl)-2-piperidinyl]-1,4-butanediol 1-benzoate (XV), as a clear, colorless oil (1.05 g; 56.9%) and the 1,4-diol, 1-[3,4,5-tris (phenylmethoxy)-6-[(phenylmethoxy)methyl]-1-(phenylmethyl) -2-piperidinyl]-1,4-butanediol (XVIII), as a yellow oil (0.41 g; 24.9%). Compound (XV): IR(neat) 1720 cm-1 (C=0); MS (FAB-MNBA) 806 (MH+), 788 (MH+H2O); 1H nmr (CDCl3) δ 1.5-1.9 (m, 2H), 2.8 (t, 1H), 3.4 (t, 2H), 3.5 (m, 1H), 3.7-4.2 (m, 7H), 4.3-4.4 (m, 1H), 4.4 (s, 2H), 4.5-4.9 (m, 7H), 5.4-5.5 (m, 1H), 7.0-7.4 (m, 27H), 7.5 (m, 1H), 8.1 (m, 2H).

Workup

  1. temperatureAfter cooling to 0° C.
  2. temperaturethe suspension was heated
  3. temperatureunder reflux for 1 hour
  4. temperatureUpon cooling to room temperature
  5. extractionextracted with ether (2×40 mL)
  6. washThe combined organic solution was washed with saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customThe solvent was evaporated under reduced pressure
  10. customthe crude residual oil was purified via flash chromatography (silica gel; 1:2 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-8cf93f8489f7468ab40071073cff51d8
Source dataset
uspto-grants-1991_07
Patent number
US05028614

Reaction notes

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