Water → 3-(8-Ethyl-naphthalen-1-yl)-propane-1,2-diamine

HRID 1159183노트

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HRID 1159183 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH2:7][CH:8]([CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[CH2:22][CH3:23])[CH:15]=[CH:14][CH:13]=1)[C:9]#[N:10].O.[OH-].[Na+]>C1COCC1>[CH2:22]([C:20]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:21]=1[C:12]([CH2:11][CH:8]([NH2:7])[CH2:9][NH2:10])=[CH:13][CH:14]=[CH:15]2)[CH3:23]

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57543207HCID 57543207, 화합물

생성물 1

HCID 575431993-(8-Ethyl-naphthalen-1-yl)-propane-1,2-diamine수율 28.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

A suspension of LiAlH4 (117 mg) in THF (2 ml) was cooled to 0° C. and treated under an argon atmosphere with a solution of (RS)-2-amino-3-(8-ethyl-naphthalen-1-yl)-propionitrile (230 mg) in THF (4 ml). The reaction mixture was stirred for 5 hrs at r.t., then treated sequentially at 0° C. with 0.1 ml H2O, 0.1 ml 4N NaOH and 0.5 ml H2O. After stirring for 30 min, the solid was filtered off and washed with THF. The filtrate was concentrated. The crude product was isolated by column chromatography (silica gel; eluent: CH2Cl2→CH2Cl2/MeOH 9:1) to give 3-(8-ethyl-naphthalen-1-yl)-propane-1,2-diamine (66 mg) as light brown oil. MS (ISP): 229.3 ((M+H)+).

후처리

  1. stirringAfter stirring for 30 min
  2. filtrationthe solid was filtered off
  3. washwashed with THF
  4. concentrationThe filtrate was concentrated
  5. customThe crude product was isolated by column chromatography (silica gel; eluent: CH2Cl2→CH2Cl2/MeOH 9:1)

출처 및 근거

ORD 기록
ord-a09cb40fce2e47bc9bbdc71fc9fed21a
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812047B2

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