1-BOC-3-PIPERIDINECARBOXALDEHYDE Chemical Properties

Boiling point:

295.4±33.0 °C(Predicted)

Density 

1.114±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

form 

liquid

pka

-2.29±0.40(Predicted)

color 

Clear, light yellow

Sensitive 

Air Sensitive

InChI

InChI=1S/C11H19NO3/c1-11(2,3)15-10(14)12-6-4-5-9(7-12)8-13/h8-9H,4-7H2,1-3H3

InChIKey

CTVHINDANRPFIL-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCCC(C=O)C1

CAS DataBase Reference

118156-93-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,N,Xn

Risk Statements 

36/37/38-50-36-22

Safety Statements 

26-36/37/39-61-37

RIDADR 

UN3077

HS Code 

29333990

1-BOC-3-PIPERIDINECARBOXALDEHYDE Usage And Synthesis

Chemical Properties

Colorless liquid

Uses

1-Boc-piperidine-3-carboxaldehyde is used as an organic chemical synthesis intermediate.

Synthesis

General procedure for the synthesis of 1-Boc-3-piperidinecarboxaldehyde from tert-butyl 3-(hydroxymethyl)piperidine-1-carboxylate: a solution of dimethylsulfoxide (DMSO, 0.18 mL, 2.6 mmol) in dichloromethane (CH2Cl2, 5 mL) was slowly added dropwise at -78 °C to a solution of oxalyl chloride (2 M in CH2Cl2, 0.65 mL, 1.3 mmol ) in a solution of methylene chloride (4 mL). The reaction mixture was stirred at -68 °C for 15 min. Subsequently, tert-butyl 3-(hydroxymethyl)piperidine-1-carboxylate (0.22 g, 1.0 mmol) was added dropwise to a dichloromethane (4 mL) solution. After continued stirring at -78 °C for 15 min, triethylamine (Et3N, 6 mL) was added. The reaction mixture was warmed to room temperature and stirred for 16 hours. Upon completion of the reaction, water was added to quench the reaction and the mixture was extracted with ether. The organic layers were combined, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to give the yellow oily product 1-Boc-3-piperidinecarboxaldehyde (0.20 g, 92% yield). The crude product could be directly used in the subsequent reaction without further purification. Mass spectrum (ESI) m/z 214 (M + 1).

References

[1] Patent: WO2006/62465, 2006, A1. Location in patent: Page/Page column 40
[2] Patent: US2004/229864, 2004, A1. Location in patent: Page/Page column 11
[3] Patent: US2017/313683, 2017, A1. Location in patent: Paragraph 0560-0561
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 4, p. 1368 - 1373
[5] Patent: US2014/31354, 2014, A1. Location in patent: Paragraph 0421; 0422

1-BOC-3-PIPERIDINECARBOXALDEHYDE(118156-93-7)Related Product Information

• 1-N-Boc-2-piperidinecarboxaldehyde,1-Boc-2-Piperidinecarboxaldehyde
• 1-BOC-4-PIPERIDINECARBOXALDEHYDE,1-N-Boc-4-piperidinecarboxaldehyde
• 1-TERT-BUTYL 2-METHYL PIPERIDINE-1,2-DICARBOXYLATE
• N-BOC-3-Aminopiperidine
• N-Boc-4-piperidinemethanol
• (+/-)-1-N-BOC-PIPERIDINE-2-CARBOXAMIDE
• N-BOC-piperidine-4-carboxylic acid
• N-Boc-2-piperidinecarboxylic acid
• Ethyl N-Boc-piperidine-4-carboxylate
• Ethyl 1-Boc-piperidine-2-carboxylate
• 1-Boc-3-hydroxypiperidine
• N-Boc-Piperidine-4-carboxylic acid methyl ester
• N-Boc-piperidine-3-methanol
• N-Boc-piperidine-2-methanol
• TERT-BUTYL 4-(AMINOCARBONYL)TETRAHYDROPYRIDINE-1(2H)-CARBOXYLATE
• 1-Boc-4-Methylaminopiperidine
• 1-N-BOC-PIPERIDINE-3-CARBOXAMIDE
• 1-Boc-3-piperidone