Cyclopropanecarboxylic acid, 2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-, (1R-trans)- (9CI) synthesis

13synthesis methods

Product Name:Cyclopropanecarboxylic acid, 2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-, (1R-trans)- (9CI)
CAS Number:153861-53-1
Molecular formula:C10H17NO4
Molecular Weight:215.25

Carbamic acid, N-[[(1S,2S)-2-(hydroxymethyl)cyclopropyl]methyl]-, 1,1-dimethylethyl ester

1262755-28-1
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Cyclopropanecarboxylic acid, 2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-, (1R-trans)- (9CI)

153861-53-1
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Yield: 84%

Reaction Conditions:

Stage #1:N-tert-butoxycarbonyl[(1S,2S)-2-(aminomethyl)cyclopropyl]methanol with Dess-Martin periodane in dichloromethane at 0 - 20; for 2 h;
Stage #2: with sodium chlorite;sodium dihydrogenphosphate dihydrate;2-methyl-but-2-ene in water;tert-butyl alcohol at 20; for 13 h;

Steps:

5 (1R,2R)-1-(N-t-Butoxycarbonyl)aminomethyl-2-carboxycyclopropane (18)
General procedure: A solution of 17 (1.8 g, 4.1 mmol) in aqueous AcOH (80%, 41 mL) was stirred at room temperature for 16 h, and then H₂O was added.
The resulting solution was extracted with AcOEt, and the organic layer was washed with saturated aqueous NaHCO₃ and brine, dried (Na₂SO₄), and evaporated.
The residue was purified by column chromatography (silica gel; hexane/AcOEt, 3:1-1:5) to give an oil (709 mg).
A mixture of the oil and Dess-Martin periodinane (1.7 g, 4.0 mmol) in CH₂Cl₂ (35 mL) was stirred at 0 °C for 1 h and then at room temperature for 1 h.
After addition of a mixture of saturated aqueous Na₂S₂O and saturated aqueous NaHCO₃ (1:1), the resulting mixture was extracted with CHCl₃, and the organic layer was washed with brine, dried (Na₂SO₄), and evaporated.
The residue was purified by column chromatography (silica gel; hexane/AcOEt, 3:1-1:1) to give an oil (700 mg).
A mixture of the oil, 2-methyl-2-butene (3.0 mL), NaClO₂ (1.3 mg, 14 mmol), and NaH₂PO₄·2H₂O (1.1 g, 7.0 mmol) in t-BuO/H₂O H (4:1, 35 mL) was stirred at room temperature for 13 h.
After addition of saturated NaCl, the resulting mixture was extracted with CHCl₃, and the organic layer was dried (Na₂SO₄), and evaporated.
The residue was purified by column chromatography (silica gel; hexane/AcOEt, 2:1-1:2) to give 18 (724 mg, 3.4 mmol, 84%) as an oil: ¹H NMR (500 MHz, CDCl₃) δ 0.86-0.94 (1H, m, H-3), 1.23-1.26 (1H, m, H-3), 1.44 (9H, s, -C(CH₃)₃), 1.51-1.54 (1H, m, H-2), 1.62-1.67 (1H, m, H-1), 3.02-3.04 (1H, m, H-1'), 3.18-3.21 (1H, m, H-1'), 4.70 and 5.70 (1H, br, -NH); ¹³C NMR (125 MHz, CDCl₃) δ 14.2, 18.7, 23.1, 28.3, 43.0, 79.6, 155.8, 179.4.

References:

Nakada, Kazuaki;Yoshikawa, Mamie;Ide, Soichiro;Suemasa, Akihiro;Kawamura, Shuhei;Kobayashi, Takaaki;Masuda, Eiji;Ito, Yoshihiko;Hayakawa, Wataru;Katayama, Takahiro;Yamada, Shizuo;Arisawa, Mitsuhiro;Minami, Masabumi;Shuto, Satoshi [Bioorganic and Medicinal Chemistry,2013,vol. 21,# 17,p. 4938 - 4950]

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