(3-HYDROXYMETHYL-PYRIDIN-4-YL)-CARBAMIC ACID TERT-BUTYL ESTER synthesis
- Product Name:(3-HYDROXYMETHYL-PYRIDIN-4-YL)-CARBAMIC ACID TERT-BUTYL ESTER
- CAS Number:407623-72-7
- Molecular formula:C11H16N2O3
- Molecular Weight:224.26
116026-93-8
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Yield:407623-72-7 63%
Reaction Conditions:
with sodium tetrahydroborate in methanol at 20; for 1 h;
Steps:
5.1.29. tert-Butyl [3-(hydroxymethyl)pyridin-4-yl]carbamate (15A)
tert-Butyl (3-formylpyridin-4-yl)carbamate12 M.C. Venuti, R.A. Stephenson, R. Alvarez, J.J. Bruno and A.M. Strosberg, J. Med. Chem. 31 (1988), p. 2136. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (60)12 was dissolved in MeOH (10 mL), and NaBH4 (205 mg, 5.43 mmol) was added. After the mixture was stirred at room temperature for 1 h, the solvent was distilled off in vacuo. The residue was partitioned between CH2Cl2 (50 mL) and brine (50 mL). Organic phase was dried over Na2SO4 and concentrated in vacuo. Obtained solid was washed with hexane to obtain the title compound (382 mg, 1.70 mmol, 63%) as a white solid. 1H NMR (CDCl3) δ: 1.53 (9H, s), 4.66 (2H, s), 7.93 (1H, s), 8.08 (1H, d, J = 5.9 Hz), 8.28 (1H, d, J = 5.9 Hz), 8.32 (1H, s). ESI-MS m/z: 225 (M+H)+.
References:
Mochizuki, Akiyoshi;Nagata, Tsutomu;Kanno, Hideyuki;Suzuki, Makoto;Ohta, Toshiharu [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 5,p. 1623 - 1642] Location in patent:experimental part
24424-99-5
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138116-34-4
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16135-36-7
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7418-65-7
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