TERT-BUTYL 4-(3-HYDROXYPROPYL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE Chemical Properties

Boiling point:

339.8±15.0 °C(Predicted)

Density 

1.029

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

15.16±0.10(Predicted)

form 

Low-Melting Solid

color 

White to Off-White

InChI

InChI=1S/C13H25NO3/c1-13(2,3)17-12(16)14-8-6-11(7-9-14)5-4-10-15/h11,15H,4-10H2,1-3H3

InChIKey

OXPWHPCCUXESFQ-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC(CCCO)CC1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

Hazard Note 

Irritant

HS Code 

2933399990

TERT-BUTYL 4-(3-HYDROXYPROPYL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE Usage And Synthesis

Uses

tert-Butyl 4-(3-Hydroxypropyl)piperidine-1-carboxylate is a reagent in the preparation of 1-alkyloxy-2-methoxy-4-nitrobenzene fragments: potent human glutaminyl cyclase inhibitors.

Synthesis

The general procedure for the synthesis of N-BOC-4-(3'-hydroxypropyl)-piperidine from 3-(4-piperidinyl)-1-propanol and di-tert-butyl dicarbonate was as follows: 1. Di-tert-butyl dicarbonate (3.66 g, 16.8 mmol) was slowly added to a stirring solution of anhydrous dichloromethane (20 mL) of 3-(4-piperidinyl)-1-propanol (1.60 g, 11.2 mmol) under nitrogen protection and the reaction was carried out at ambient temperature. 2. The resulting reaction mixture was stirred continuously for 2 hours. 3. Upon completion of the reaction, the mixture was purified directly by silica gel column chromatography with the eluent being methanol in dichloromethane (0-3% gradient). 4. The target fraction was collected to afford N-BOC-4-(3'-hydroxypropyl)-piperidine as a clear oil (2.40 g, 88% yield).

References

[1] Organic Letters, 2002, vol. 4, # 4, p. 549 - 552
[2] Patent: US2008/306082, 2008, A1. Location in patent: Page/Page column 5-6
[3] Patent: US6235731, 2001, B1
[4] Organic and Biomolecular Chemistry, 2014, vol. 12, # 5, p. 783 - 794
[5] Tetrahedron, 1999, vol. 55, # 39, p. 11619 - 11639

TERT-BUTYL 4-(3-HYDROXYPROPYL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE(156185-63-6)Related Product Information

• TERT-BUTYL 4-(3-HYDROXYPROPYL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE
• piperidine-4-propanol
• METHYL N-BOC-4-PIPERIDINEPROPIONATE
• 4-(2-ETHOXYCARBONYL-ACETYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• N-Boc-4-piperidinepropionic acid
• TERT-BUTYL FORMATE
• N-BOC-1-OXA-8-AZA-SPIRO[4.5]DECAN-3-OL
• ETHYL 3-(1-BOC-PIPERIDINE-4-YL)-DL-BETA-ALANINATE
• N-ALPHA-FMOC-BETA-(1-BOC-PIPERIDIN-4-YL)-D,L-ALANINE
• 4'-N-BOC-SPIRO-INDANE-PIPERIDINE-3-CARBOXYLIC ACID
• 4-[2-CARBOXY-1-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-ETHYL]-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• 4-(2-ETHOXYCARBONYL-1-ACETYL)-PIPERIDINE-1-CARBOXYLIC ACID TERTIO-BUTYL ESTER
• (S)-N-ALPHA-N'-DI-T-BUTYLOXYCARBONYL-4-PIPERIDYLALANINE
• L-ALA-4PIP(BOC)-OME
• BOC-(3S, 3R)-3-AMINO-[3-(4-PIP(BOC))]PROPIONIC ACID
• 4-(1-BENZYLOXYCARBONYLAMINO-2-CARBOXY-ETHYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• 2-(1-(TERT-BUTOXYCARBONYL)PIPERIDIN-4-YL)CYCLOHEXANECARBOXYLIC ACID
• 4-(1-AMINO-2-CARBOXY-ETHYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER