Hydrogen Peroxide → HCID 67111221, compound

HRID 537372Notes

Reaction equation

HRID 537372 reaction equation
C[O:2][C:3]1([C:42]2[CH:58]=[CH:57][CH:56]=[CH:55][C:43]=2[O:44][CH2:45]CCC2(C(O)=O)CCC2)[CH2:8][CH2:7][N:6]([C:9]([C@]2(OC3C=C(C(F)(F)F)SC=3)CCCN(C(=O)C3C(C(F)(F)F)=CC=CN=3)[C@@H]2CCC)=[O:10])[CH2:5][CH2:4]1.[OH-:59].[Na+].OO.[CH2:63]1C[O:66][CH2:65][CH2:64]1>B1C2CCCC1CCC2>[OH:2][C:3]1([C:42]2[CH:58]=[CH:57][CH:56]=[CH:55][C:43]=2[O:44][CH3:45])[CH2:4][CH2:5][N:6]([C:9]([O:10][CH2:3][C:42]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:43]=2)=[O:59])[CH:7]([CH2:63][CH2:64][CH2:65][OH:66])[CH2:8]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 86669386HCID 86669386, compound

Product 1

HCID 67111221HCID 67111221, compound

Reagents, catalysts & solvents 1

HCID 789669-Borabicyclo(3.3.1)nonaneSolvent

Procedure

To a solution of benzyl 2-allyl-4-hydroxy-4-(2-methoxyphenyl)piperidine-1-carboxylate 131 (220 mg, 0.58 mmol) in THF (2 mL), 0.5 M of 9-BBN in THF (3.5 mL) was added. The reaction solution was stirred at r.t for 16 hr and then 10% NaOH (3 mL) and H2O2 (3 mL) were added. After stirring for 30 mins, the reaction mixture was extracted with ethyl acetate. After removal of solvent, the crude product was purified by silica gel chromatography (gradient, 30% to 75% EtOAc/hexanes) to give benzyl 4-hydroxy-2-(3-hydroxypropyl)-4-(2-methoxyphenyl)piperidine-1-carboxylate 132. LC/MS RT (2.25 min method)=1.228 min. Mass observed: 400.2 (M+H).

Workup

  1. stirringAfter stirring for 30 mins
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. customAfter removal of solvent
  4. customthe crude product was purified by silica gel chromatography (gradient, 30% to 75% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ec89088ed91748f490c99eb35eff8fca
Source dataset
uspto-grants-2014_10
Patent number
US08859776B2

Reaction notes

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