1-Tetralone → 1,2,3,4-Tetrahydro-2-naphthalenol

HRID 1637058ノート

反応式

HRID 1637058 の反応式
[C:1]([C@:5]1(N)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]1[C@H:11](O)[CH3:12])([CH3:4])(C)C.C1CC(=[O:24])C2C(=CC=CC=2)C1>C1COCC1>[CH2:12]1[CH:4]([OH:24])[CH2:1][C:5]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:11]1

参加物

4

反応物 2

HCID 107241-TetraloneHCID 86754982(1R, 2S)-2-tert-butyl-2-aminophenylethanol

生成物 1

HCID 107471,2,3,4-Tetrahydro-2-naphthalenol収率 915.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

Borane methylsulfide complex (neat, ~10M, 0.44 mL, 4.4 mmol) was added to a solution of (1R, 2S)-2-tert-butyl-2-aminophenylethanol [Angew. Chem. Int. Ed. Engl. 26 1141 (1987)] (120 mg, 0.62 mmol) in THF (22 mL) at ambient temperature and stirred for 16 hrs. α-Tetralone (906 mg, 6.2 mmol) as a solution in THF (3 mL) was added to the preceding solution over a 1 hr, stirred for 15 min after addition was completed, cooled to 0° C., and quenched with methanol (20 mL). After stirring the quenched reaction for 18 hrs, the solvents were removed under vacuum, the residual oil was dissolved in methylene chloride (30 mL), washed with pH 4 phosphate buffer (30 mL), water (30 mL), treated with magnesium sulfate, and the solvent was removed under vacuum to give the (R) tetralol 841 mg (91% yield) 82% ee.

後処理

  1. stirringstirred for 15 min
  2. additionafter addition
  3. customquenched with methanol (20 mL)
  4. stirringAfter stirring
  5. customthe quenched reaction for 18 hrs
  6. customthe solvents were removed under vacuum
  7. dissolutionthe residual oil was dissolved in methylene chloride (30 mL)
  8. washwashed with pH 4 phosphate buffer (30 mL), water (30 mL)
  9. additiontreated with magnesium sulfate
  10. customthe solvent was removed under vacuum

出典と根拠

ORDレコード
ord-579d8f36b8e64514b3178a7d52565126
出典データセット
uspto-grants-2000_03
特許番号
US06037505

反応ノート

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