Hydrogen Peroxide → (S)-4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-alpha, alpha-dimethylbenzeneacetic acid, ethyl ester

HRID 266398Notes

Reaction equation

HRID 266398 reaction equation
B(Cl)([C@H]1[C@H](C)[C@H]2C(C)(C)[C@@H](C2)C1)[C@H]1[C@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1.[OH:23][C:24]([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[CH:25]1[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33][C:34]([C:36]2[CH:41]=[CH:40][C:39]([C:42]([CH3:49])([CH3:48])[C:43]([O:45][CH2:46][CH3:47])=[O:44])=[CH:38][CH:37]=2)=[O:35])[CH2:27][CH2:26]1.O.OO>O1CCCC1>[OH:23][C:24]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[CH:25]1[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33][C@@H:34]([C:36]2[CH:41]=[CH:40][C:39]([C:42]([CH3:48])([CH3:49])[C:43]([O:45][CH2:46][CH3:47])=[O:44])=[CH:38][CH:37]=2)[OH:35])[CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 9958564Ethyl 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-alpha,alpha-dimethylbenzeneacetateHCID 20642586(-)-B-chlorodiisopinocamphenylboran

Product 1

HCID 12074743(S)-4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-alpha, alpha-dimethylbenzeneacetic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve (-)-B-chlorodiisopinocamphenylborane (2.5 g, 7.8 mmol) in anhydrous tetrahydrofuran (5 mL). Add a solution of 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α, α-dimethylbenzeneacetic acid, ethyl ester (2 g, 3.54 mmol) in anhydrous tetrahydrofuran (5 mL). Stir at room temperature for 3 days and cool to 0° C. Add water (1 mL) and 30% hydrogen peroxide (2 mL) and stir for 20 minutes. Add methylene chloride (30 mL) and wash with brine (30 mL), then aqueous sodium hydrogen carbonate (30 mL), then brine (30 mL). Dry (MgSO4), evaporate the solvent in vacuo and purify by chromatography to give the title compound.

Workup

  1. temperaturecool to 0° C
  2. washAdd methylene chloride (30 mL) and wash with brine (30 mL)
  3. dry with materialDry (MgSO4)
  4. customevaporate the solvent in vacuo
  5. custompurify by chromatography

Sources & evidence

ORD record
ord-a64ce35339a04417b726645a118d76db
Source dataset
uspto-grants-1997_07
Patent number
US05650516

Reaction notes

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