Water → HCID 71239740, 화합물

HRID 587125노트

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HRID 587125 반응식
[BH4-].[Na+].[CH2:3]([O:10][CH:11]1[CH2:16][CH2:15][C:14]([C:22]#[N:23])([C:17](OCC)=[O:18])[CH2:13][CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O>C1COCC1.O.C1COCC1>[CH2:3]([O:10][CH:11]1[CH2:16][CH2:15][C:14]([CH2:17][OH:18])([C:22]#[N:23])[CH2:13][CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 71239678HCID 71239678, 화합물

생성물 1

HCID 71239740HCID 71239740, 화합물수율 116.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 21881883Oxolane--water (1/1)용매

실험 절차

To a solution of sodium borohydride (186 mg, 4.92 mmol, 2.5 equiv) in THF/H2O (5/0.5 mL) was added a solution of ethyl 4-(benzyloxy)-1-cyanocyclohexanecarboxylate (565 mg, 1.97 mmol, 1.0 equiv) in THF (dry, 3 mL) dropwise. The reaction mixture was stirred at room temperature for 18 hrs. It was concentrated to give the white solid. H2O (20 mL) was added. The aqueous phase was extracted with EtOAc (4×30 mL). The combined organic solution was washed with brine (30 mL), dried over anhydrous Na2SO4 and then concentrated to give 565 mg of crude 4-(benzyloxy)-1-(hydroxymethyl)cyclohexanecarbonitrile as a colorless sticky oil which was not purified and submitted for the next reaction.

후처리

  1. concentrationIt was concentrated
  2. customto give the white solid
  3. extractionThe aqueous phase was extracted with EtOAc (4×30 mL)
  4. washThe combined organic solution was washed with brine (30 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b79e2a669da64a5c9ca0ec84cab1682b
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09226923B2

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