Acetic Acid → 1-Oxododecyl-3-hydroxypiperidine

HRID 2395714ノート

反応式

HRID 2395714 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 152303421-Oxododecyl-3-hydroxypiperidine

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
75 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c0d228bc748942b0bd24dc2e018ff071
出典データセット
uspto-grants-1996_02
特許番号
US05489600

反応ノート

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