Water → HCID 178484843、化合物

HRID 25534

反応式

HRID 25534 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O[C:15](=O)[NH:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([OH:23])[CH2:19][CH2:18]1)C1C=CC=CC=1.[O-]S([O-])(=O)=O.[Na+].[Na+].O>C1COCC1>[CH3:15][NH:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([OH:23])[CH2:19][CH2:18]1

参加物

6

反応物 4

HCID 962WaterHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 178523817HCID 178523817、化合物

生成物 1

HCID 178484843HCID 178484843、化合物収率 46%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of 37.9 g (0.94 mol, 2.0 eq) LAH in 1.3 l THF was added a suspension of 117 g (0.47 mol) trans-4-Hydroxy-cyclohexylcarbamic acid benzyl ester in 11 THF over a period of 6 h via a cannula keeping the temperature between 5-10° C. The reaction was refluxed over night and a mixture of Na2SO4, silica gel and water (160 g, 50 g, 80 ml) was added, stirred for additional 30 min, filtered and concentrated. The crude material was titurated with hexane to yield 27.9 g (46%) trans-4-Methylamino-cyclohexanol. Column chromatography of the mother liquor on silica gel yielded additional 17.1 g (28%) trans-4-Methylamino-cyclohexanol as white solid, MS: 129 (MH+) (in analogy to Venuti, Michael C.; Jones, Gordon H.; Alvarez, Robert; Bruno, John J.; J.Med.Chem.; 30; 2; 1987; 303-318).

後処理

  1. additionwas added
  2. custombetween 5-10° C
  3. temperatureThe reaction was refluxed over night
  4. additionwas added
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-48fa585817f74c2fa874d0d25871e2e2
出典データセット
uspto-grants-2005_02
特許番号
US06858651B2

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