Acetic Acid → 1-Oxododecyl-3-hydroxypiperidine

HRID 2395714Notes

Reaction equation

HRID 2395714 reaction equation
[O:1]=[C:2]([N:14]1[CH2:19][CH2:18][CH2:17][CH:16]([O:20][Si](C(C)(C)C)(C)C)[CH2:15]1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C(O)(=O)C.O1CCCC1.[OH-].[Na+]>O>[O:1]=[C:2]([N:14]1[CH2:19][CH2:18][CH2:17][CH:16]([OH:20])[CH2:15]1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 189895461-oxododecyl-3-(O-tert-butyldimethylsilyoxy)piperidine

Product 1

HCID 152303421-Oxododecyl-3-hydroxypiperidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

Mix 1-oxododecyl-3-(O-tert-butyldimethylsilyloxy)piperidine (3.5 mmol) with a solution of acetic acid (9 mL), tetrahydrofuran (6 mL) and water (6 mL). Heat at 75° C. overnight. Cool to room temperature and make basic with cold 10% sodium hydroxide and extract into methylene chloride. Wash with water, then with brine and dry (Na2SO4). Evaporate the solvent in vacuo and purify by flash chromatography (5% methanol/methylene chloride) to give the title compound.

Workup

  1. temperatureCool to room temperature
  2. extractionextract into methylene chloride
  3. washWash with water
  4. dry with materialwith brine and dry (Na2SO4)
  5. customEvaporate the solvent in vacuo
  6. custompurify by flash chromatography (5% methanol/methylene chloride)

Sources & evidence

ORD record
ord-c0d228bc748942b0bd24dc2e018ff071
Source dataset
uspto-grants-1996_02
Patent number
US05489600

Reaction notes

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