Aluminum(III) Chloride → 2-(3-(Di(propan-2-yl)amino)-1-phenylpropyl)-4-(hydroxymethyl)phenol

HRID 131772

반응식

HRID 131772 반응식
[CH:1]([N:4]([CH:27]([CH3:29])[CH3:28])[C:5](=O)[CH2:6][CH:7]([C:14]1[CH:19]=[C:18]([C:20](OC)=[O:21])[CH:17]=[CH:16][C:15]=1[O:24]C)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.[Cl-].[Al+3].[Cl-].[Cl-]>O1CCCC1>[CH:27]([N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6][CH:7]([C:14]1[CH:19]=[C:18]([CH2:20][OH:21])[CH:17]=[CH:16][C:15]=1[OH:24])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:29])[CH3:28]

참가 물질

5

반응물 3

HCID 6451240Aluminum(III) ChlorideHCID 12972418(+/-)-N,N-diisopropyl-3-(2-methoxy-5-methoxycarbonylphenyl)-3-phenylpropionamideHCID 68718528lithium aluminium hydride THF

생성물 1

HCID 99279712-(3-(Di(propan-2-yl)amino)-1-phenylpropyl)-4-(hydroxymethyl)phenol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of (±)-N,N-diisopropyl-3-(2-methoxy-5-methoxycarbonylphenyl)-3-phenylpropionamide (0.79 g, 2.0 mmol) in 20 ml of tetrahydrofuran was cooled to 5° C. and then treated with 2.5 ml of 1M LiAlH4/THF. After stirring at room temperature for 18 hrs. finely powdered aluminium chloride (0.3 g) was added and stirring was continued for additional 4 hrs. The reaction was quenched at 5° C. by the dropwise addition of water followed by aqueous sodium hydroxide solution. The mixture was diluted with diethyl ether (150 ml) and the organic phase was washed with half saturated brine, dried (sodium sulphate), and evaporated to dryness to give the title compound as a solid off-white foam. Tlc (2) 0.16, m.p. 48-51° C. A portion of the material was converted into the hydrochloride (ethereal hydrochloric acid), m.p. 186-189° C. (dec.).

후처리

  1. stirringstirring
  2. waitwas continued for additional 4 hrs
  3. customThe reaction was quenched at 5° C. by the dropwise addition of water
  4. additionThe mixture was diluted with diethyl ether (150 ml)
  5. washthe organic phase was washed with half saturated brine
  6. dry with materialdried (sodium sulphate)
  7. customevaporated to dryness

출처 및 근거

ORD 기록
ord-d541b03b426d4683ab8d85ed2033ec83
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384980B2

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