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

HRID 2065926Notes

Reaction equation

HRID 2065926 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

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).

Workup

  1. customreaction with a catalyst

Sources & evidence

ORD record
ord-ba536c6933704c298692dc6140f60cad
Source dataset
uspto-grants-2012_10
Patent number
US08288565B2

Reaction notes

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