Tetrahydrofuran → 2-trimethylsilylethyl (3RS,4RS)-4-(3-bromophenyl)-3-(2-trimethylsilyl-ethoxycarbonyloxy)-piperidine-1-carboxylate

HRID 1004928ノート

反応式

HRID 1004928 の反応式
C([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Br:20])[CH:15]=2)[CH:10](O)[CH2:9]1)C1C=CC=CC=1.[C:22](=[O:25])([O-:24])[O-:23].[Li+].[Li+].Cl[C:29]([O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])=[O:30].O1[CH2:42][CH2:41]CC1>C1(C)C=CC=CC=1>[Br:20][C:16]1[CH:15]=[C:14]([CH:11]2[CH2:10][CH2:9][N:8]([C:29]([O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])=[O:30])[CH2:13][CH:12]2[O:25][C:22]([O:24][CH2:41][CH2:42][Si:34]([CH3:36])([CH3:35])[CH3:33])=[O:23])[CH:19]=[CH:18][CH:17]=1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 11125Lithium CarbonateHCID 109101682-(Trimethylsilyl)ethyl chloroformateHCID 22127354(3RS,4RS)-1-benzyl-4-(3-bromophenyl)-piperidin-3-ol

生成物 1

HCID 539146402-trimethylsilylethyl (3RS,4RS)-4-(3-bromophenyl)-3-(2-trimethylsilyl-ethoxycarbonyloxy)-piperidine-1-carboxylate収率 43%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
-50 °C

実験手順

A solution of 691 mg (2.00 mmol) of (3RS,4RS)-1-benzyl-4-(3-bromophenyl)-piperidin-3-ol in 3 ml of absolute tetrahydrofuran was treated with 163 mg (2.20 mmol) of lithium carbonate and cooled to -50° C. A solution of 722 mg (4.00 mmol) of β-trimethylsilylethyl chloroformate [Synthesis 346 (1987)] in 4 ml of toluene was added dropwise thereto at -50° C. The reaction mixture was warmed to room temperature and stirred for 24 hours. Subsequently, the mixture was partitioned between methylene chloride and water, the organic phase was dried over magnesium sulphate and finally the solvent was removed under reduced pressure. The crude product (0.8 g) was purified by chromatography on silica gel with methylene chloride as the eluent. There were obtained 470 mg (43% of theory) of 2-trimethylsilylethyl (3RS,4RS)-4-(3-bromophenyl)-3-(2-trimethylsilylethoxycarbonyloxy)-piperidine-1-carboxylate as a light yellow oil, which was used directly in the next step.

後処理

  1. customat -50° C
  2. temperatureThe reaction mixture was warmed to room temperature
  3. customSubsequently, the mixture was partitioned between methylene chloride and water
  4. dry with materialthe organic phase was dried over magnesium sulphate
  5. customfinally the solvent was removed under reduced pressure
  6. customThe crude product (0.8 g) was purified by chromatography on silica gel with methylene chloride as the eluent

出典と根拠

ORDレコード
ord-639babbb1ef742d69741c7efc3835537
出典データセット
uspto-grants-2000_04
特許番号
US06051712

反応ノート

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