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

HRID 612973노트

반응식

HRID 612973 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 107471,2,3,4-Tetrahydro-2-naphthalenol수율 915.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-945b0bbd05e24a3aa967df5521194e6e
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06005133

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