Water → HCID 71239740、化合物

HRID 587125ノート

反応式

HRID 587125 の反応式
[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

参加物

6

反応物 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 71239678HCID 71239678、化合物

生成物 1

HCID 71239740HCID 71239740、化合物収率 116.9%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 21881883Oxolane--water (1/1)溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b79e2a669da64a5c9ca0ec84cab1682b
出典データセット
uspto-grants-2016_01
特許番号
US09226923B2

反応ノート

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