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

HRID 1246920노트

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HRID 1246920 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-71500117350e40bf885c8952e0a52074
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129228B2

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