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

HRID 1159183

反応式

HRID 1159183 の反応式
[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]

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57543207HCID 57543207、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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)+).

後処理

  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)

出典と根拠

ORDレコード
ord-a09cb40fce2e47bc9bbdc71fc9fed21a
出典データセット
uspto-grants-2010_10
特許番号
US07812047B2

関連ノート

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