Acetic Acid → HCID 15295385, compound

HRID 2395712Notes

Reaction equation

HRID 2395712 reaction equation
[O:1]=[C:2]([N:14]1[CH2:19][CH2:18][CH:17]([O:20][Si](C(C)(C)C)(C)C)[CH2:16][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[CH2:15][CH2:16][CH:17]([OH:20])[CH2:18][CH2:19]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 18989543HCID 18989543, compound

Product 1

HCID 15295385HCID 15295385, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

Mix 1-oxododecyl-4-(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 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. 587E-115

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-9b5a0aabe3094bc1ba32c0bc6dbf6f1c
Source dataset
uspto-grants-1996_02
Patent number
US05489600

Reaction notes

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