Sodium borohydride → rel-(1R,5R)-5-Methyl-3-(3-nitro-4-pyridinyl)-2-cyclohexen-1-ol

HRID 879157노트

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HRID 879157 반응식
[CH3:1][CH:2]1[CH2:7][C:6](=[O:8])[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[CH2:3]1.[BH4-].[Na+]>CCO>[CH3:1][C@@H:2]1[CH2:7][C@H:6]([OH:8])[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[CH2:3]1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 592265435-Methyl-3-(3-nitro-4-pyridinyl)-2-cyclohexen-1-one

생성물 1

HCID 59226572rel-(1R,5R)-5-Methyl-3-(3-nitro-4-pyridinyl)-2-cyclohexen-1-ol수율 94%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
0 °C

실험 절차

To a solution of 5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enone (1.0 equiv.) in EtOH (0.3 M) was added CeCl3-7H2O (1.2 equiv.). The reaction was cooled to 0° C., then NaBH4 (1.2 equiv.) was added in portions. Stirred for 1 h at 0° C., then quenched by adding water, concentrated to remove the EtOH, added EtOAc, extracted the organics, washed with brine, then dried with Na2SO4, filtered and concentrated to yield cis-(+/−)-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol (94%). LC/MS=235.2 (M+H), LC=2.62 min.

후처리

  1. customquenched
  2. additionby adding water
  3. concentrationconcentrated
  4. customto remove the EtOH
  5. additionadded EtOAc
  6. extractionextracted the organics,
  7. washwashed with brine
  8. dry with materialdried with Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-144253bd462d41cdb34e06c062c2fd23
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987457B2

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