Benzyl chloroformate → Benzyl 3-(hydroxymethyl)azepane-1-carboxylate

HRID 988799ノート

反応式

HRID 988799 の反応式
C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]([CH2:14][OH:15])[CH2:8]1.[CH2:16]([O:23][C:24](Cl)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1.O>[CH2:16]([O:23][C:24]([N:7]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]([CH2:14][OH:15])[CH2:8]1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

5

反応物 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 21901984(Azepan-3-yl)methanol

生成物 1

HCID 20598086Benzyl 3-(hydroxymethyl)azepane-1-carboxylate収率 94%

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

反応条件

温度
0 °C

実験手順

Potassium carbonate was added to a mixture of azepan-3-yl-methanol (145) (0.032 g, 0.2485 mmol) in THF/H2O (2:1, 0.31 mL). The suspension was cooled to 0° C., and (benzyloxy)carbonyl chloride (0.071 mL, 0.497 mmol) was added dropwise. The reaction was allowed to warm to room temperature overnight, and was then concentrated in vacuo. CH2Cl2 and H2O were added. The organics were extracted, washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by automated silica gel chromatography with 75:25 Hexanes:EtOAc to obtain 3-Hydroxymethyl-azepan-1-carboxylic acid benzyl ester (146) in approximately 94% yield.

後処理

  1. temperatureto warm to room temperature overnight
  2. concentrationwas then concentrated in vacuo
  3. additionCH2Cl2 and H2O were added
  4. extractionThe organics were extracted
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by automated silica gel chromatography with 75:25 Hexanes

出典と根拠

ORDレコード
ord-3c16bc67256a4cac82e3c4131498f35e
出典データセット
uspto-grants-2003_10
特許番号
US06635661B2

反応ノート

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