tert-Butyl 3-Oxopiperidine-1-carboxylate (1-Boc-3-piperidone) CAS 206551-43-1 98% Pale Yellow to Colorless Oil or Low-Melting Solid | N-Boc Protecte

1. Product Overview

tert-Butyl 3-oxopiperidine-1-carboxylate (CAS 206551-43-1), commonly called 1-Boc-3-piperidone, has molecular formula C₁₀H₁₇NO₃ and MW 199.25 g/mol. It is a six-membered saturated N-heterocycle with a Boc-protected nitrogen at the 1-position and a ketone at the 3-position. The ketone undergoes reduction (to alcohol), condensation (with amines → enamines, with hydrazines → pyrazoles), or Wittig-type olefination. The Boc group is cleanly removed with TFA or 4 M HCl/dioxane to afford 3-piperidone hydrochloride. Used as a key scaffold in the construction of substituted piperidines.

2. Key Features and Benefits

• β-Keto Piperidine Core: The 3-keto enables enamine formation, Grignard addition, or reductive amination after deprotection.

• Boc Protection: Stable to base and nucleophiles; orthogonal to Fmoc/Cbz; removed under mild acid.

• Versatile Intermediate: After deprotection → 3-piperidone for N-alkylation, reductive amination, or spirocycle formation.

• High Purity: Supplied ≥98% (HPLC/GC), suitable for library synthesis and medicinal chemistry support.

3. Major Applications

• Organic Synthesis: Reduction of the 3-keto to equatorial/axial alcohols (NaBH₄, L-Selectride); condensation with arylamines → enamines for cyclization.

• Heterocycle Formation: Reaction with hydrazines → 3-piperidonyl pyrazoles; with o-phenylenediamine → fused diazepines (methodology studies).

• Library / SAR Studies: Introduces the 3-substituted piperidine motif after deprotection and functionalization.

• Protecting Group Strategy: Demonstrates Boc orthogonality in polyfunctional N-heterocycle sequences.

• Analytical Reference: Standard for HPLC/LC-MS method development in piperidone derivative profiling.

4. Technical Specifications

Item Description
Product Name tert-Butyl 3-Oxopiperidine-1-carboxylate (1-Boc-3-piperidone)
Synonyms 1-Boc-3-piperidone; N-Boc-3-oxopiperidine; 1-Piperidinecarboxylic acid, 3-oxo-, 1,1-dimethylethyl ester
CAS Number 206551-43-1
Molecular Formula C₁₀H₁₇NO₃
Molecular Weight 199.25 g/mol
MDL Number MFCD02179141
PubChem CID 9929088
Assay (Purity) ≥98% (HPLC)
Appearance Colorless to pale yellow oil or low-melting solid (mp < RT)
Boiling Point ~110–115 °C / 0.5 mmHg (Estimated)
Density ~1.06–1.09 g/mL at 25 °C
Refractive Index n²⁰/D ≈ 1.470–1.475
Calculated LogP ~1.2–1.6
Polar Surface Area (PSA) 46.6 Ų
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 4 (C=O Boc ×2, ketone O, N)
Rotatable Bonds 2
Solubility Soluble in DCM, THF, ethyl acetate, methanol, DMSO; insoluble in water/hexane.
SMILES CC(C)(C)OC(=O)N1CCC(=O)CC1
InChI Key InChIKey (PubChem): efgRTYUI—verify via database; actual: YJKVNBEHWERFSH-UHFFFAOYSA-N
Actual PubChem InChIKey:YJKVNBJEWERFSH-UHFFFAOYSA-N
InChI Key (PubChem) YJKVNBJEWERFSH-UHFFFAOYSA-N
Storage 2–8 °C, sealed, protect from moisture & light; stable ≥18–24 months if unopened
HS Code 2933.59.90 / 3822.90.00

5. Storage and Handling

Store in a tightly sealed container at 2–8 °C, protected from moisture and light. The β-ketoamide is stable as a neat oil/solid but may slowly enolize or discolor on prolonged air exposure—store under inert atmosphere if long-term. For Boc deprotection: TFA/DCM (1:4, 15–30 min, rt), then concentrate and neutralize if needed. Ketone reduction with NaBH₄ in MeOH (0 °C → rt). Standard PPE recommended.

6. Safety Summary

• GHS Classification: GHS07 – Warning

• Signal Word: Warning

• Hazard Statements: H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation)

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