Methanol → [(1S,2S)-2-aminocyclohexyl]methanol

HRID 2065926ノート

反応式

HRID 2065926 の反応式
Cl.[NH:2]1[C@@H:10]2[C@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)C[C@H]1C(OCC1C=CC=CC=1)=O.[CH3:21][OH:22]>[Pd]>[NH2:2][C@H:10]1[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]1[CH2:21][OH:22]

参加物

4

反応物 2

HCID 887Methanol2 回HCID 116450511H-Indole-2-carboxylic acid, octahydro-, phenylmethyl ester, hydrochloride (1:1), (2S,3aR,7aS)-

生成物 1

HCID 10154065[(1S,2S)-2-aminocyclohexyl]methanol

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

実験手順

In yet another embodiment, (2S,3aR,7aS)-benzyl octahydro-1H-indole-2-carboxylate hydrochloride salt (3), is produced using a starting material of crystalline ((1S,2S)-2-(S)-1-phenylethylamino)cyclohexyl)methanol (11). The first step of the process involves reaction with a catalyst including palladium on carbon in the presence of methanol to produce ((1S,2S)-2-aminocyclohexyl)methanol (17). Compound (17) is subjected to treatment with sodium cyanide in the presence of formaldehyde to produce compound (18). Subsequently, compound (18) is first reacted with trimethylsilyl chloride, and then the product of that reaction is treated with benzyl chloride to produce compound (19). Further, compound (19) is subjected to three sequential reactions to produce compound (20) as illustrated in FIG. 3. Specifically, compound (19) is first subjected to treatment with hydrochloric acid. Subsequently, methanesulfonyl chloride is added to the reaction mixture. Thereafter, potassium hydroxide is added to the reaction to produce compound (20). After compound (20) is produced, the compound is treated with aqueous mineral acid to produce the hydrochloride salt of compound (5).

後処理

  1. customreaction with a catalyst

出典と根拠

ORDレコード
ord-ba536c6933704c298692dc6140f60cad
出典データセット
uspto-grants-2012_10
特許番号
US08288565B2

反応ノート

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