Water → HCID 178484843, 화합물

HRID 25534

반응식

HRID 25534 반응식
[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

참가 물질

6

반응물 4

HCID 962WaterHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 178523817HCID 178523817, 화합물

생성물 1

HCID 178484843HCID 178484843, 화합물수율 46%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-48fa585817f74c2fa874d0d25871e2e2
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858651B2

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