917099-02-6

Basic information

• Product Name: (2R,4S)-FMOC-4-HYDROXYPIPERIDINE-2-CARBOXYLIC ACID
• Synonyms: (2R,4S)-FMOC-4-HYDROXYPIPERIDINE-2-CARBOXYLIC ACID;(2R,4S)-1-(((9H-Fluoren-9-yl)Methoxy)carbonyl)-4-hydroxypiperidine-2-carboxylic acid
• CAS NO: 917099-02-6
• Molecular Formula: C21H21NO5
• Molecular Weight: 367.4
• Mol File: 917099-02-6.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (2R,4S)-FMOC-4-HYDROXYPIPERIDINE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4S)-FMOC-4-HYDROXYPIPERIDINE-2-CARBOXYLIC ACID(917099-02-6)
• EPA Substance Registry System: (2R,4S)-FMOC-4-HYDROXYPIPERIDINE-2-CARBOXYLIC ACID(917099-02-6)

Safety Data

• Hazardous Substances Data: 917099-02-6(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 1844-40-2 (2S,4R)-4-hydroxypiperidine-2-carboxylic acid 
• 653589-10-7 1,2-di-tert-butyl (2S)-4,6-dioxopiperidine-1,2-dicarboxylate 
• 653589-35-6 di(tert-butyl) (2S,4R)-4-hydroxy-1,2-piperidinedicarboxylate 
• 653589-16-3 di(tert-butyl) (2S,4S)-4-hydroxy-6-oxo-1,2-piperidinedicarboxylate 
• 4382-31-4 (2S,4S)-4-hydroxy-2-piperidinecarboxylic acid 
• 653589-44-7 di(tert-butyl) (2S,4S)-4-hydroxy-1,2-piperidinedicarboxylate 

Relevant articles and documents

Synthesis of Enantiopure 4-Hydroxypipecolate and 4-Hydroxylysine Derivatives from a Common 4,6-Dioxopiperidinecarboxylate Precursor

tert-Butyl 2-substituted 4,6-dioxo-1-piperidinecarboxylates 4 have been prepared in good yield starting from Boc-Asp-OtBu and other β-amino acids. By analogy with chiral tetramic acids, their reduction by NaBH4 in CH2Cl2/AcOH afforded the corresponding cis-4-hydroxy δ-lactams in good yield and stereoselectivity (68-98% de). In the absence of the A(1,3) strain (reduction of 6-substituted 2,4-dioxo-1-piperidines 7), the cis-4-hydroxy isomer was still obtained as the major product but the de values were consistently lower. 4-Hydroxy-6-oxo- 1,2-piperidinedicarboxylate 2a, readily accessible from Boc-Asp-OtBu (three steps, 63% overall yield), has proven to be an excellent building block for the synthesis of cis- and trans-4-hydroxypipecolates 17 and 24 (52 and 36% overall yield, respectively) and for the synthesis of a protected 4-hydroxylysine derivative 29 (41% overall yield).