tert-Butanol → tert-butyl (1S,3R)-3-acetyl-2,2-dimethylcyclobutane-1-carboxylate

HRID 2179740ノート

反応式

HRID 2179740 の反応式
[C:1]([C@@H:4]1[CH2:7][C@H:6]([C:8]([OH:10])=[O:9])[C:5]1([CH3:12])[CH3:11])(=[O:3])[CH3:2].C1COCC1.C1CCC(N=C=NC2CCCCC2)CC1.[C:33](O)([CH3:36])([CH3:35])[CH3:34]>CCOC(C)=O>[C:1]([C@@H:4]1[CH2:7][C@H:6]([C:8]([O:10][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:9])[C:5]1([CH3:12])[CH3:11])(=[O:3])[CH3:2]

参加物

6

反応物 4

HCID 6386tert-ButanolHCID 8028TetrahydrofuranHCID 10868DicyclohexylcarbodiimideHCID 10630987(1S,3R)-3-acetyl-2,2-dimethylcyclobutane-1-carboxylic acid

生成物 1

HCID 21576610tert-butyl (1S,3R)-3-acetyl-2,2-dimethylcyclobutane-1-carboxylate収率 70%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred ice cooled solution of (1S,3R)-3-acetyl-2,2-dimethylcyclobutanecarboxylic acid (16.0 g, 94.117 mmol) in THF (160 ml) DMAP (1.148 g, 9.409 mmol) and DCC (23.265 g, 112.93 mmol) were added, followed by t-butyl alcohol (27.63 ml, 282.34 mmol) was added drop wise. The reaction mixture was stirred at room temperature for 36 hours. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with EtOAc and filtered through a celite bed and washed with EtOAc. The filtrate was as such concentrated and purified by silica gel column (100-200 mesh, elution 10% EtOAc in hexane) to afford the title compound as a solid. Wt: 15.0 g: Yield: 70%; 1H NMR (300 MHz, CDCl3): δ 2.86-2.74 (m, 1H), 2.70-2.50 (m, 2H), 2.04 (s, 3H), 1.89-1.78 (m, 1H), 1.42, 1.40 (2s, 12H), 0.91 (s, 3H); Mass: [M+Na]+ 249 (100%).

後処理

  1. additionwas added drop wise
  2. customAfter completion of the reaction (monitored by TLC)
  3. filtrationfiltered through a celite bed
  4. washwashed with EtOAc
  5. concentrationas such concentrated
  6. custompurified by silica gel column (100-200 mesh, elution 10% EtOAc in hexane)

出典と根拠

ORDレコード
ord-d13f62ef13df4444948a3f32e6e360ae
出典データセット
uspto-grants-2015_06
特許番号
US09067966B2

反応ノート

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