Detail of "6859-99-0"

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CAS Number:
6859-99-0
Name:
3-Hydroxypiperidine
Molecular Structure:
Formula:
C₅H₁₁NO
Molecular Weight:
101.15
Synonyms:
3-Hydroxyhexahydropyridine;NSC 62082;
EINECS:
229-957-4
Density:
1.016 g/cm³
Melting Point:
56-60 °C
Boiling Point:
191.9 °C at 760 mmHg
Flash Point:
104.5 °C
Solubility:
soluble in water
Appearance:
White to light yellow crystalline powder and lumps
Hazard Symbols:
Xi, C
Risk Codes:
34-20/21/22-36/37/38
Safety:
26-36/37/39-45-27 Details
Transport Information:
UN 3263 8/PG 2

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Reference

Asymmetric Synthesis of (+)-L-733,060 and (+)-CP-99,994 Based on a New Chiral 3-Piperidinol Synthon: Asymmetric Synthesis of (+)-L-733,060 and (+)-CP-99,994 Based on a New Chiral 3-Piperidinol Synthon. Huang, Pei-Qiang; Liu, Liang-Xian; Wei, Bang-Guo; Ruan, Yuan-Ping ( Department of Chemistry, Xiamen University, Xiamen, Fujian 361005, Peop. Rep. China). Organic Letters, 5(11), 1927-1929 (English) 2003 American Chemical Society. CODEN: ORLEF7. ISSN: 1523-7060. DOCUMENT TYPE: Journal CA Section: 27 (Heterocyclic Compounds (One Hetero Atom)) Selective and potent neurokinin substance P receptor antagonists (+)-L-733,060 and (+)-CP-99,994 have been synthesized starting from a new (3S)-piperidinol synthon derived from L-glutamic acid. The methods featured a C-2 regioselective redn. of a glutarimide, Lewis acid-promoted Si to C-2 Ph group migration, and stereoselective redn. of an acetylated oxime as the key steps.

Syntheses of (S)-(-)-3-piperidinol from L-glutamic acid and (S)-malic acid: Syntheses of (S)-(-)-3-piperidinol from L-glutamic acid and (S)-malic acid. Olsen, Richard K.; Bhat, Krishna L.; Wardle, Robert B.; Hennen, William J.; Kini, Ganesh D. (Dep. Chem. Biochem., Utah State Univ., Logan, UT 84322, USA). J. Org. Chem., 50(6), 896-9 (English) 1985. CODEN: JOCEAH. ISSN: 0022-3263. DOCUMENT TYPE: Journal CA Section: 27 (Heterocyclic Compounds (One Hetero Atom)) (S)-(-)-3-Piperidinol (I) has been prepd. by 2 independent routes beginning with (S)-(-)-malic acid and L-(+)-glutamic acid, resp. The known (S)-(+)-5-hydroxy-4-pentanolide (II), obtainable from L-(+)-glutamic acid, was converted, via the corresponding tosylate, to the previously reported azidolactone III. Catalytic redn. of the azido group yielded (S)-5-hydroxy-2-piperidinone, which was readily reduced to I by treatment with borane in THF.Several reagents such as 94944-67-9 is used here. The synthesis of I from the pentanolide II was effected in 4 steps and in an overall yield of 37%. (S)-(-)-Malic acid was transformed to the known acetonide triol IV, which was converted via a sequence to tosylation, displacement with cyanide ion, and redn. of the nitrile, to the cryst. amino diol V (R = R1 = H, Z = PhCH2O2C) (VI). The cyclization of tosylate V (R = tosyl, R1 = tetrahydropyranyl, Z = PhCH2O2C) obtained from VI by activation and protection, to the protected piperidinol VII proved to be erratic and to proceed in only fair to poor yields. Deprotection of VII gave the chiral piperidinol I in an overall yield, and proceeding in 10 steps from triol IV, of 10%. .

Detail of "6859-99-0"

3-Hydroxypiperidine

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