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

HRID 2179730노트

반응식

HRID 2179730 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 21576610tert-butyl (1S,3R)-3-acetyl-2,2-dimethylcyclobutane-1-carboxylate수율 60%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매3회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-495752057c604441a786dd4dfa7c7d40
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067966B2

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