Methyl chloroformate → 2-Dipropylamino-8-methoxycarbonyl-1,2,3,4-tetrahydronaphthalene

HRID 274797노트

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HRID 274797 반응식
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH2:8][CH2:7]2.C([Li])CCC.CCCCCC.Cl[C:31]([O:33][CH3:34])=[O:32]>O1CCCC1.C(=O)(O)[O-].[Na+]>[CH2:13]([N:12]([CH2:16][CH2:17][CH3:18])[CH:9]1[CH2:8][CH2:7][C:6]2[C:11](=[C:2]([C:31]([O:33][CH3:34])=[O:32])[CH:3]=[CH:4][CH:5]=2)[CH2:10]1)[CH2:14][CH3:15]

참가 물질

7

반응물 4

HCID 6586Methyl chloroformateHCID 8058HexaneHCID 145295648-Bromo-2-dipropylamino-1,2,3,4-tetrahydronaphthaleneHCID 178418339Butyllithium

생성물 1

HCID 101082452-Dipropylamino-8-methoxycarbonyl-1,2,3,4-tetrahydronaphthalene수율 63.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 516892Sodium Bicarbonate용매

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온도
-78 °C

실험 절차

Alternatively, to a solution of 8-bromo-2-dipropylamino-1,2,3,4-tetrahydronaphthalene (220 mg, 0.71 mMol) in tetrahydrofuran (5 mL) at -78° C. was added a solution of n-butyl lithium in hexane (1.6 M, 1 mL, 1.6 mMol), and the solution was stirred for two hours at -78° C. The solution was then cannulated into a solution of methyl chloroformate (0.5 mL, 6.5 mMol) in tetrahydrofuran (10 mL) at -78° C., and the reaction mixture was allowed to warm gradually to room temperature. The reaction mixture was diluted with saturated aqueous sodium bicarbonate and was then extracted with diethyl ether. The combined extracts were dried over sodium sulfate and evaporated in vacuo to give a greenish-yellow oil. Purification by flash chromatography (3:1 hexane:tetrahydrofuran+tr. NH4OH) gave the title compound as a colorless glass (130 mg, 63%). The hydrochloride salt was formed and recrystallized (acetone/diethyl ether) to give colorless crystals (m.p.=132° C.).

후처리

  1. temperatureto warm gradually to room temperature
  2. extractionwas then extracted with diethyl ether
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. customevaporated in vacuo
  5. customto give a greenish-yellow oil
  6. customPurification by flash chromatography (3:1 hexane:tetrahydrofuran+tr. NH4OH)

출처 및 근거

ORD 기록
ord-32dd8015b42d47f3a5701d39217337df
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05389687

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