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

HRID 988799노트

반응식

HRID 988799 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-3c16bc67256a4cac82e3c4131498f35e
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06635661B2

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