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Triphenylphosphine → 6-((S)-1-imidazol-1-ylmethyl-2-methyl-propoxy)-5-nitro-3,4-dihydro-2H-naphthalen-1-one

HRID 496431
ノート
印刷プレビュー

反応式

HRID 496431 の反応式
[OH:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[N:16]1([CH2:21][C@H:22](O)[CH:23]([CH3:25])[CH3:24])[CH:20]=[CH:19][N:18]=[CH:17]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.CO.C(Cl)Cl>[N:16]1([CH2:21][C@@H:22]([O:1][C:2]2[C:3]([N+:13]([O-:15])=[O:14])=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]3)[CH:23]([CH3:25])[CH3:24])[CH:20]=[CH:19][N:18]=[CH:17]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 123928306-Hydroxy-5-nitro-3,4-dihydronaphthalen-1(2H)-oneHCID 60029931(R)-1-imidazol-1-ylmethyl-2-methyl-propanol

生成物 1

HCID 697352806-((S)-1-imidazol-1-ylmethyl-2-methyl-propoxy)-5-nitro-3,4-dihydro-2H-naphthalen-1-one収率 69.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 21226129Dichloromethane methanol溶媒

実験手順

To a solution of 6-hydroxy-5-nitro-1-tetralone (0.888 g, 4.29 mmol) in dry THF (10 mL) was added (R)-1-imidazol-1-ylmethyl-2-methyl-propanol (0.737 g, 4.78 mmol) followed by triphenylphospine (1.26 g, 4.78 mmol). After approximately 10 min, diethylazodicarboxylate (0.75 mL, 4.78 mmol) was added slowly. The reaction was allowed to stir at RT for 2 days. The reaction mixture was concentrated under reduced pressure and the residue was purified by chromatography (SiO2, 20% acetone/CH2Cl2 then 5% MeOH/CH2Cl2) afforded the title compound as a foam (1.02 g, 2.97 mmol, 69%). The structure was confirmed by NMR and mass spectrometry. MS m/z 344 (M++H). 2. 5-Amino-6-((S)-1-imidazol-1-ylmethyl-2-methyl-propoxy)-3,4-dihydro-2H-naphthalen-1-one

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by chromatography (SiO2, 20% acetone/CH2Cl2

出典と根拠

ORDレコード
ord-7b908bd77cb24f70bebf8b93d49664ea
出典データセット
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06943183B2

反応ノート

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