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Citation: Fang Jiaobing, Chen Yuchen, Cui Haonan, Wang Shiyu, Liu Mingzhe. Synthesis of trans-4-(Hydroxymethyl)piperidin-3-ol[J]. Chemistry, ;2019, 82(7): 663-665. shu

Synthesis of trans-4-(Hydroxymethyl)piperidin-3-ol

School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016

Corresponding author: Liu Mingzhe, mz_liu03@163.com
Received Date: 5 March 2019
Accepted Date: 12 April 2019

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Trans-4-(hydroxymethyl)piperidin-3-ol, a key intermediate of novel 5-hydroxytryptamine receptor agonist candidate, was synthesized by 4-hydroxymethylpyridin as starting material through four reaction steps including benzyl group protection, reduction with sodium borohydride, hydroboration-oxidation, deprotection of benzyl group. The total yield was up to 55.7%. The reaction products were characterized by IR, ¹H NMR and MS, and the synthetic process was also optimized.
- Trans-4-(hydroxymethyl)piperidin-3-ol,
- Hydroboration-oxidation,
- 5-Hydroxytryptamine receptor agonist,
- Benzyl protection
1. [1]
  Y Sakurai-Yamashita, K Yamashita, M Yoshimura et al. Life Sci., 2000, 66(1):31~34.
2. [2]
  K Y Chan, R De Vries, F P J Leijten et al. Eur. J. Pharm., 2009, 619(1~3):61~67.
3. [3]
  T Bach, T Syversveen, A M Kvingedal et al. Naunyn-Schmiedeberg's Arch. Pharm., 2001, 363(2):146~160.
4. [4]
5. [5]
6. [6]
  R W Mc Callum. Am. J. Gastroenterol., 1991, 86(2):135~149.
7. [7]
8. [8]
  S Mohammad, Z Zhou, Q Gong. Am. J. Physiol. Heart C, 1997, 273(5):H2534~H2538.
9. [9]
  E Farrington. Pediatric Nurs., 1996, 22(3):256~256.
10. [10]
  J H De Maeyer, N H Prins, J A Schuurkes et al. Pharmacol. Exp. Ther., 2006, 317(3):955~964.
11. [11]
  J H De Maeyer, R Straetemans R, J A Schuurkes et al. Br. J. Pharmacol., 2006, 147(2):140~157.
12. [12]
  W Chai, K Y Chan, R De Vries et al. Life Sci., 2012, 90(13~14):538~544.
13. [13]
  H J M Gijsen, M J A De Cleyn et al. Tetrahedron, 2008, 64(10):2456~2464.
1. [1]
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2. [2]
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