Cyclohexanecarboxylic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, methyl ester, (1S,2R)- synthesis
- Product Name:Cyclohexanecarboxylic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, methyl ester, (1S,2R)-
- CAS Number:267230-26-2
- Molecular formula:C13H23NO4
- Molecular Weight:257.33
67-56-1
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Yield:267230-26-2 95%
Reaction Conditions:
with diazomethyl-trimethyl-silane in diethyl ether;benzene at 25; for 0.666667 h;
Steps:
31.a
A 2.0 M solution of (trimethylsilyl)diazomethane in diethyl ether (5.0 mL, 10.0 mmol) was added over 10 min to a solution of (S,2R)-2-tert- butoxycarbonylamino-1-cyclohexanecarboxylic acid (0.994 g, 4.09 mmol; purchased from νeoMPS) in a 1:1 mixture of benzene and methanol (50 mL) at 25 0C. The resulting mixture was stirred at 25 0C for 30 min, and then was partitioned between half-saturated sodium bicarbonate solution (150 mL) and ethyl acetate (2 x 150 mL). The combined organic layers were dried over sodium sulfate, decanted, and were concentrated in vacuo to afford the desired product, (lS,2R)-2-tert- butoxycarbonylamino-1-cyclohexanecarboxylic acid methyl ester (1.00 g, 3.89 mmol, 95%), as a colorless oil. 1H νMR (400 MHz, CDCl3) δ: 1.44 (9H, s), 1.58 - 1.68 (3H, m), 1.72 - 1.81 (2H, m), 1.98 - 2.05 (2H, m), 2.77 - 2.80 (IH, m), 3.69 (3H, s), 3.82 - 3.90 (IH, m), 5.29 - 5.31 (IH, m). LC-MS (ESI) calcd for Ci3H23NO4 257.16, found 258.2 [M+H+].
References:
WO2008/73982,2008,A2 Location in patent:Page/Page column 158
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