Hydrochloric Acid → Methyl (1R,3S,4S)-3-amino-4-hydroxycyclopentane-1-carboxylate hydrochloride

HRID 2244661Notes

Reaction equation

HRID 2244661 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([NH:10]C(OC(C)(C)C)=O)[C@@H:7]([OH:18])[CH2:6]1)=[O:4].[ClH:19]>O1CCOCC1>[ClH:19].[CH3:1][O:2][C:3]([C@H:5]1[CH2:6][C@H:7]([OH:18])[C@@H:8]([NH2:10])[CH2:9]1)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 7022354(1S,2S,4R)-N-Boc-1-amino-2-hydroxycyclopentane-4-carboxylic acid methyl ester

Product 1

HCID 68685176Methyl (1R,3S,4S)-3-amino-4-hydroxycyclopentane-1-carboxylate hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (1S,2S,4R)—N—Boc-1-amino-2-hydroxycyclopentane-4-carboxylic acid methyl ester (0.2 g) in 4M HCl in dioxane (4 ml) was stirred under an argon atmosphere at r.t. for 2 hrs. The reaction mixture was concentrated to give (1R,3S,4S)-3-amino-4-hydroxy-cyclopentanecarboxylic acid methyl ester hydrochloride (165 mg, contains some dioxane) as light brown gum. MS: 160.4 ([M+H]+).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-dabb708bc1f4466eaffd0e598cd5fac3
Source dataset
uspto-grants-2010_03
Patent number
US07678917B2

Reaction notes

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