Hydrogen Peroxide → HCID 21955351, compound

HRID 514809Notes

Reaction equation

HRID 514809 reaction equation
C1C[O:4]CC1.[CH2:6]([C:9]1([OH:22])[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)[CH:7]=[CH2:8].[OH-].[Na+].OO>O>[OH:22][C:9]1([CH2:6][CH2:7][CH2:8][OH:4])[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21955339Tert-butyl 4-allyl-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 21955351HCID 21955351, compoundYield 117.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of BH3 in THF (21 mL, 21.0 mmol) was added slowly to a mixture of tert-butyl 4-allyl-4-hydroxypiperidine-1-carboxylate (500 mg, 2.07 mmol) and THF (5 L) at 0° C. under nitrogen, and then stirred for 30 min. The resulting mixture was allowed to warm to room temperature and stirred overnight. The mixture was cooled to 0° C. and 3N sodium hydroxide (1 mL) was added followed by the addition of 30% hydrogen peroxide (1 mL). The resulting mixture was allowed to warm to room temperature and stirred for 2.5 hours. The mixture was then treated with water (10 mL) and extracted with EA (3×20 mL). The combined organic extracts were dried over Na2SO4 and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel with (30% EtOAc/PE) to give tert-butyl 4-hydroxy-4-(3-hydroxypropyl) piperidine-1-carboxylate 13B (629 mg) as a colorless oil. 1H NMR (CHLOROFORM-d) δ: 3.65 (t, J=5.7 Hz, 4H), 3.36 (br. s., 2H), 3.16 (br. s., 2H), 1.63-1.71 (m, 2H), 1.53-1.62 (m, 4H), 1.41-1.48 (m, 9H).

Workup

  1. stirringstirred overnight
  2. temperatureThe mixture was cooled to 0° C.
  3. temperatureto warm to room temperature
  4. stirringstirred for 2.5 hours
  5. extractionextracted with EA (3×20 mL)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. customthe solvent was removed in vacuo
  8. customThe residue was purified by column chromatography on silica gel with (30% EtOAc/PE)

Sources & evidence

ORD record
ord-9abdffdf1c1549669e9824c6b23ac7be
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Reaction notes

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