Aluminium lithium hydride → HCID 178486030, 화합물

HRID 2057269노트

반응식

HRID 2057269 반응식
C([O:3][C:4](=O)[CH:5]=[CH:6][CH2:7][CH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH3:16])[CH2:11][CH2:10]1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CO.C1COCC1.[Pd]>[C:20]([O:19][C:17](=[O:18])[N:15]([C@H:12]1[CH2:11][CH2:10][C@H:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][OH:3])[CH2:14][CH2:13]1)[CH3:16])([CH3:21])([CH3:23])[CH3:22]

참가 물질

6

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 178471411HCID 178471411, 화합물

생성물 1

HCID 178486030HCID 178486030, 화합물수율 97%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2.45 g (7.2 mmol) trans-5-[4-(tert-Butoxycarbonyl-methyl-amino)-cyclohexyl]-pent-2-enoic acid ethyl ester and 200 mg of Pd/C (10%) in 40 ml MeOH was stirred for 20 h under H2-atmosphere. After filtration and evaporation of the methanol under vacuo, 2.39 g 5-[4-(tert-Butoxy carbonyl-methyl-amino)-cyclohexyl]-pentanoic acid ethyl ester could be isolated. 2.05 g (6.0 mmol) of this ester and 470 mg (12 mmol) of LiAlH4 were stirred in 20 ml of THF at RT for 5 h. Exess of LiAlH4 was destroyed by adding 10 ml of EtOAc and by carefully dropping brine to the reaction-mixture. The solution was dissolved in ether and washed with 1N HCl and water. The organic phase was concentrated under reduced pressure yielding 1.75 g (97%) of clean trans-[4-(5-Hydroxy pentyl)-cyclohexyl)-methyl-carbamic acid tert-butyl ester, MS: 300 (MH+).

후처리

  1. filtrationAfter filtration and evaporation of the methanol under vacuo, 2.39 g 5-[4-(tert-Butoxy carbonyl-methyl-amino)-cyclohexyl]-pentanoic acid ethyl ester
  2. customcould be isolated
  3. customExess of LiAlH4 was destroyed
  4. additionby adding 10 ml of EtOAc
  5. dissolutionThe solution was dissolved in ether
  6. washwashed with 1N HCl and water
  7. concentrationThe organic phase was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-2301559deec0484e877b92db1a112c27
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07335687B2

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