4-(Aminomethyl)cyclohexanone, N-BOC protected → HCID 86647903, 화합물

HRID 707057노트

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HRID 707057 반응식
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[CH3:17][Mg]Br>O1CCCC1>[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][CH:9]1[CH2:10][CH2:11][C:12]([OH:15])([CH3:17])[CH2:13][CH2:14]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 404240274-(Aminomethyl)cyclohexanone, N-BOC protectedHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 86647903HCID 86647903, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

A solution of tert-butyl(4-oxocyclohexyl)methylcarbamate (1.00 g) was dissolved in tetrahydrofuran (20 mL) and cooled to −78° C. Methylmagnesium bromide (4.40 mL) was added dropwise. The reaction was stirred for 2 hours at −78° C. then allowed to warm to 0° C. and stirred for 30 minutes. The resulting suspension was quenched with water (10 mL), diluted with ether (50 mL), washed with ammonium chloride (25 mL), washed with brine (25 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography (Reveleris 80 g) eluting using a gradient of 5% to 50% ethyl acetate/dichloromethane over 30 minutes (flow=60 mL/min) gave the title compound as a 2:1 mixture of cis and trans isomers.

후처리

  1. temperatureto warm to 0° C.
  2. stirringstirred for 30 minutes
  3. customThe resulting suspension was quenched with water (10 mL)
  4. additiondiluted with ether (50 mL)
  5. washwashed with ammonium chloride (25 mL)
  6. washwashed with brine (25 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washSilica gel chromatography (Reveleris 80 g) eluting
  11. customover 30 minutes

출처 및 근거

ORD 기록
ord-9895707da33945b2a94b35b15629b01c
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174982B2

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