Sodium Hydroxide → 1-(Cyclohexylamino)-1-(hydroxymethyl)cyclopentane

HRID 276258

반응식

HRID 276258 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Al+3].[Cl-].[Cl-].[Cl-].[CH2:11]1[C:15]2([NH:24][C:18]3([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[O:17][CH2:16]2)[CH2:14][CH2:13][CH2:12]1.[OH-].[Na+]>C1COCC1.O>[CH:18]1([NH:24][C:15]2([CH2:16][OH:17])[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 1831620513-Oxa-6-azadispiro[4.1.5.2]tetradecaneHCID 21226445Aluminium lithium hydride

생성물 1

HCID 183161421-(Cyclohexylamino)-1-(hydroxymethyl)cyclopentane수율 79%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
20 °C

실험 절차

To a solution of LiAlH4 (0.93 g, 24.4 mmol) and AlCl3 (3.24 g, 24.4 mmol) in THF at 4° C. was added dropwise a solution of 14-aza-7-oxadispiro[4.2.5.1]tetradecane (2.38 g, 12,2 mmol) in THF (15 mL). The resulting mixture was warmed to 20° C. and stirred for 45 min., then cooled to 4° C. Water (5 mL) was slowly added to quench the reaction and a 1N NaOH solution (85 mL) was added to dissolve the resulting solids. The resulting solution was extracted with Et2O (200 mL). The organic layer was dried (Na2SO4) and concentrated under reduced pressure to yield 1-(cyclohexylamino)-1-(hydroxymethyl)cyclopentane 1.89 g (79%): GC-MS m/z 197 (M+).

후처리

  1. temperaturecooled to 4° C
  2. customto quench
  3. customthe reaction
  4. dissolutionto dissolve the resulting solids
  5. extractionThe resulting solution was extracted with Et2O (200 mL)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6e68bfb8a2134a28b6bf190ddde2c6b9
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06353006B1

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