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

HRID 2065926노트

반응식

HRID 2065926 반응식
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]

참가 물질

4

반응물 2

HCID 887Methanol2회HCID 116450511H-Indole-2-carboxylic acid, octahydro-, phenylmethyl ester, hydrochloride (1:1), (2S,3aR,7aS)-

생성물 1

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

시약·촉매·용매 1

HCID 23938Palladium촉매

실험 절차

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).

후처리

  1. customreaction with a catalyst

출처 및 근거

ORD 기록
ord-ba536c6933704c298692dc6140f60cad
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288565B2

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