4-(Aminomethyl)cyclohexanone, N-BOC protected → HCID 86647903、化合物

HRID 707057ノート

反応式

HRID 707057 の反応式
[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]

参加物

4

反応物 2

HCID 404240274-(Aminomethyl)cyclohexanone, N-BOC protectedHCID 178418573HCID 178418573、化合物

生成物 1

HCID 86647903HCID 86647903、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9895707da33945b2a94b35b15629b01c
出典データセット
uspto-grants-2015_11
特許番号
US09174982B2

反応ノート

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