Potassium;tri(butan-2-yl)boranuide → cis-3-Hydroxy-4-(3,4-dimethylphenoxy)-1-carbobenzyloxy-piperidine

HRID 2058976

반응식

HRID 2058976 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[CH3:26])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:8][C:7]1=[O:22].C([BH-](C(CC)C)C(CC)C)(CC)C.[K+]>O1CCCC1>[OH:22][C@H:7]1[C@@H:6]([O:5][C:4]2[CH:23]=[CH:24][C:25]([CH3:26])=[C:2]([CH3:1])[CH:3]=2)[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])[CH2:8]1

참가 물질

4

반응물 2

HCID 4304157Potassium;tri(butan-2-yl)boranuideHCID 205488924-(3,4-Dimethylphenoxy)-1-carbobenzyloxy-3-piperidone

생성물 1

HCID 70544723cis-3-Hydroxy-4-(3,4-dimethylphenoxy)-1-carbobenzyloxy-piperidine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

10.0 g (0.028 mol) of the 4-(3,4-dimethylphenoxy)-1-carbobenzyloxy-3-piperidone described in Example 44 are dissolved in 60 ml of dry tetrahydrofurane and the solution is treated dropwise, at room temperature in a nitrogen atmosphere, with 112 ml of a 0.5 M solution of potassium tri-sec.-butyl-borohydride (K selectride) (0.056 mol) in tetrahydrofurane. After the addition has ended, the reaction mixture is stirred for a further 3 hours at room temperature and then concentrated to about 1/3 of the original volume under a water pump vacuum. The solution is cooled to 0° in an ice-water bath, treated dropwise with 130 ml of water and extracted by shaking with twice 150 ml of methylene chloride. The combined organic phases are washed with 0.1 N hydrochloric acid, then with 0.1 N sodium hydroxide solution and finally with water, dried over sodium sulphate and evaporated to dryness under a water pump vacuum. The oily crude product is dissolved in toluene and the solution is filtered through a layer of silica gel. cis-3-hydroxy-4-(3,4-dimethylphenoxy)-1-carbobenzyloxy-piperidine is obtained in the form of a pale yellow oil by elution with a toluene/ethyl acetate mixture (5:1).

후처리

  1. additionAfter the addition
  2. concentrationconcentrated to about 1/3 of the original volume under a water pump vacuum
  3. temperatureThe solution is cooled to 0° in an ice-water bath
  4. additiontreated dropwise with 130 ml of water
  5. extractionextracted
  6. stirringby shaking with twice 150 ml of methylene chloride
  7. washThe combined organic phases are washed with 0.1 N hydrochloric acid
  8. dry with materialwith 0.1 N sodium hydroxide solution and finally with water, dried over sodium sulphate
  9. customevaporated to dryness under a water pump vacuum
  10. dissolutionThe oily crude product is dissolved in toluene
  11. filtrationthe solution is filtered through a layer of silica gel

출처 및 근거

ORD 기록
ord-088ceacaea324fc3bd23748fde8398eb
출처 데이터셋
uspto-grants-1982_03
특허 번호
US04320137

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