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

HRID 274797ノート

反応式

HRID 274797 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
-78 °C

実験手順

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.).

後処理

  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)

出典と根拠

ORDレコード
ord-32dd8015b42d47f3a5701d39217337df
出典データセット
uspto-grants-1995_02
特許番号
US05389687

反応ノート

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