Isopropanol → (1R,2S)-2-amino-1-(quinolin-3-yl)propan-1-ol dihydrochloride

HRID 1661473

反応式

HRID 1661473 の反応式
[ClH:1].N[C@@H](C)[C@@H](C1C=CC(SC)=CC=1)O.[O:15]=[C:16]([C:27]1[CH:28]=[N:29][C:30]2[C:35]([CH:36]=1)=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@@H:17]([NH:19]C(=O)OC(C)(C)C)[CH3:18].CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].CC(O)C>C1(C)C=CC=CC=1>[ClH:1].[ClH:1].[NH2:19][C@@H:17]([CH3:18])[C@@H:16]([C:27]1[CH:28]=[N:29][C:30]2[C:35]([CH:36]=1)=[CH:34][CH:33]=[CH:32][CH:31]=2)[OH:15]

参加物

6

反応物 4

HCID 3776IsopropanolHCID 11143Aluminum isopropoxideHCID 59339907(S)-tert-butyl 1-oxo-1-(quinolin-3-yl)propan-2-ylcarbamateHCID 66688026(1R,2S)-2-amino-1-[4-(methylthio)phenyl]propan-1-ol hydrochloride

生成物 1

HCID 66686852(1R,2S)-2-amino-1-(quinolin-3-yl)propan-1-ol dihydrochloride

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Following the procedure described for preparation of 29b. Starting from (S)-tert-butyl 1-oxo-1-(quinolin-3-yl)propan-2-ylcarbamate (42c, 1.6 g, 5.33 mmol), Aluminium isopropoxide (0.68 g, 3.33 mmol) and 2-propanol (4.5 mL, 59.16 mmol) in toluene (7 mL) stirred at +50° C. in sealed reaction tube flushed with argon for 16 hours. Work up and deprotection of the intermediate BOC-protected amine afforded the subtitle compound as a colourless solid. Yield 1.29 g (88%).

後処理

  1. customflushed with argon for 16 hours

出典と根拠

ORDレコード
ord-f573b2294e3f4745b3ae7fc31bcda453
出典データセット
uspto-grants-2011_10
特許番号
US08030340B2

関連ノート

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