Diethyl Ether → (1-Acetyl-cyclobutyl)-carbamic acid tert-butyl ester

HRID 2038797ノート

反応式

HRID 2038797 の反応式
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:12](=[O:17])N(OC)C)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:19][Mg]Br.CCOCC>C1COCC1>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:12](=[O:17])[CH3:19])[CH2:9][CH2:10][CH2:11]1)([CH3:2])([CH3:3])[CH3:4]

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 86671822HCID 86671822、化合物HCID 178418573HCID 178418573、化合物

生成物 1

HCID 67508029(1-Acetyl-cyclobutyl)-carbamic acid tert-butyl ester収率 63%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

To a solution of [1-(methoxy-methyl-carbamoyl)-cyclobutyl]-carbamic acid tert-butyl ester (11.5 g, 44.6 mmol) in THF (150 mL) at 0° C. was slowly added methylmagnesium bromide as a 3.0M solution in ether (37.2 mL, 111 mmol). The reaction was allowed to slowly warm to 25° C. and stirred for 24 h then quenched by the addition of saturated aqueous NH4Cl (100 mL). EtOAc (200 mL) was added and the layers were separated. The aqueous phase was extracted two more times with EtOAc. The organic layers were combined, washed with brine, dried (Na2SO4), decanted and concentrated to afford a solid. The solid was purified via normal phase flash chromatography on silica gel (10-50% EtOAc-heptane) to afford (1-acetyl-cyclobutyl)-carbamic acid tert-butyl ester as a white solid (6.02 g, 63%).

後処理

  1. customat 0° C.
  2. customthen quenched by the addition of saturated aqueous NH4Cl (100 mL)
  3. additionEtOAc (200 mL) was added
  4. customthe layers were separated
  5. extractionThe aqueous phase was extracted two more times with EtOAc
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. customdecanted
  9. concentrationconcentrated
  10. customto afford a solid
  11. customThe solid was purified via normal phase flash chromatography on silica gel (10-50% EtOAc-heptane)

出典と根拠

ORDレコード
ord-ad3613ba72dd465d82a8cb1a46652f17
出典データセット
uspto-grants-2013_11
特許番号
US08575360B2

反応ノート

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