Potassium;tri(butan-2-yl)boranuide → (3SR,4SR)-1,4-dibenzyl-piperidin-3-ol

HRID 382789노트

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HRID 382789 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10](=[O:21])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCC(C)[BH-](C(C)CC)C(C)CC.[K+]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:10]([OH:21])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 4304157Potassium;tri(butan-2-yl)boranuideHCID 9922920(RS)-1,4-Dibenzyl-piperidin-3-one

생성물 1

HCID 18175381(3SR,4SR)-1,4-dibenzyl-piperidin-3-ol수율 72%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-70 °C

실험 절차

To a solution of 9.0 g (SR)-1,4-dibenzyl-piperidin-3-one (32 mmol) in 200 ml dry THF were added at −78° C. dropwise 48 ml K-selectride® (1 N in THF, 48 mmol). The reaction mixture was stirred for 1 h at −70° C. and then warmed to r.t. The reaction was quenched by the addition of 100 ml NaHCO3-solution and the aqueous phase was extracted twice with ethyl acetate (200 ml). The combined organic phases were washed with water (100 ml) and brine (100 ml). The organic phase was dried over MgSO4, filtrated and the solvent was removed under reduced pressure to give the crude product. Purification by chromatography (ethyl acetate/hexane 1/2 to 2/1) yielded 6.5 g of the product (23 mmol, 72%) as a yellow oil.

후처리

  1. temperaturewarmed to r.t
  2. customThe reaction was quenched by the addition of 100 ml NaHCO3-solution
  3. extractionthe aqueous phase was extracted twice with ethyl acetate (200 ml)
  4. washThe combined organic phases were washed with water (100 ml) and brine (100 ml)
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltrated
  7. customthe solvent was removed under reduced pressure
  8. customto give the crude product
  9. customPurification by chromatography (ethyl acetate/hexane 1/2 to 2/1)

출처 및 근거

ORD 기록
ord-9ad44e8221694e9dad8e8084c18a3b6d
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310213B1

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