tert-Butyl [2,2,2-trifluoro-1-(hydroxymethyl)ethyl]carbamate synthesis
- Product Name:tert-Butyl [2,2,2-trifluoro-1-(hydroxymethyl)ethyl]carbamate
- CAS Number:126536-02-5
- Molecular formula:C8H14F3NO3
- Molecular Weight:229.2
1039356-94-9
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126536-02-5
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Yield:126536-02-5 93%
Reaction Conditions:
with lithium borohydride in tetrahydrofuran at 20; for 0.5 h;
Steps:
tert-Butyl N-[2,2,2-trifluoro-1-(hydroxymethyl)ethyl]carbamate (33)
To a solution of methyl 2-(tert-butoxycarbonylamino)-3,3,3-trifluoropropanoate (0.91 g, 3.53 mmol) in THF (18 mL) was added lithium borohydride (0.23 g, 10.6 mmol, 3.0 eq). After stirring at room temperature for 30 min, the reaction mixture was poured into 1 M aqueous hydrochloric acid and extracted with chloroform. The organic layer was dried through a phase separator and concentrated under reduced pressure. The residue was purified using silica gel column chromatography (OH 10%-45% ethyl acetate in hexane) to obtain 33 (0.75 g, 3.28 mmol, 93%) as a colorless powder. 1H NMR (400 MHz, CDCl3) δ ppm 1.48 (s, 9H), 1.74 (brs, 1H), 3.80-3.89 (m, 1H), 3.90-4.00 (m, 1H), 4.21-4.43 (m, 1H), 5.16 (brs, 1H), MS (ESI/APCI dual) m/z: 252 [M+Na]+
References:
Yamaguchi-Sasaki, Toru;Kawaguchi, Takanori;Okada, Atsushi;Tokura, Seiken;Tanaka-Yamamoto, Nozomi;Takeuchi, Tomoki;Ogata, Yuya;Takahashi, Ryo;Kurimoto-Tsuruta, Risa;Tamaoki, Tomokazu;Sugaya, Yutaka;Abe-Kumasaka, Tomoko;Arikawa, Kaho;Yoshida, Ippei;Sugiyama, Hiroyuki;Kanuma, Kosuke;Yoshinaga, Mitsukane [Bioorganic and Medicinal Chemistry,2020,vol. 28,# 24,art. no. 115818] Location in patent:supporting information
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126535-90-8
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![Alanine, N-[(1,1-dimethylethoxy)carbonyl]-3,3,3-trifluoro-2-hydroxy-, ethyl ester](/CAS/20210305/GIF/126535-84-0.gif)
126535-84-0
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126536-02-5
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