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

HRID 2179730ノート

反応式

HRID 2179730 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].[CH3:13][C:14](O)([CH3:16])[CH3:15].C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1.CN(C1C=CN=CC=1)C>[C:1]([C@@H:4]1[CH2:7][C@H:6]([C:8]([O:10][C:14]([CH3:16])([CH3:15])[CH3:13])=[O:9])[C:5]1([CH3:12])[CH3:11])(=[O:3])[CH3:2]

参加物

6

反応物 3

HCID 6386tert-ButanolHCID 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 60%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a stirred ice cooled solution of (1S,3R)-3-acetyl-2,2-dimethylcyclobutanecarboxylic acid (3.0 g, 17.65 mmol) in THF (5 ml), t-BuOH (5.1 ml, 52.94 mmol) and DMAP (0.036 g, 0.176 mmol) in THF (3 ml) were added followed by DCC (4.4 g, 21.2 mmol) in dry THF (2 ml) was added slowly. Then the reaction was stirred at room temperature for about 36 hours. After completion of the reaction (monitored by TLC), the reaction mixture was filtered through a celite bed and washed with DCM. The filtrate was washed with 5% HCl, water, aqueous NaHCO3 and dried over Na2SO4. The solvent was evaporated and purified by silica gel column (60-120, elution 10% EtOAc in hexane) to afford title compound as a pale yellow syrup. Wt: 2.4 g; Yield: 60%; 1H NMR (300 MHZ, CDCl3): δ 2.84 (m, 1H), 2.70-2.51 (m, 2H), 2.06 (s, 3H), 1.89-1.80 (m, 1H), 1.41 (s, 12H), 0.93 (s, 3H); Mass: [M+Na]+ 249 (100%).

後処理

  1. additionwas added slowly
  2. customAfter completion of the reaction (monitored by TLC)
  3. filtrationthe reaction mixture was filtered through a celite bed
  4. washwashed with DCM
  5. washThe filtrate was washed with 5% HCl, water, aqueous NaHCO3
  6. dry with materialdried over Na2SO4
  7. customThe solvent was evaporated
  8. custompurified by silica gel column (60-120, elution 10% EtOAc in hexane)

出典と根拠

ORDレコード
ord-495752057c604441a786dd4dfa7c7d40
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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