Carbamic acid, [(1R)-2-hydroxy-1-(methoxymethyl)ethyl]-, 1,1-dimethylethyl synthesis

7synthesis methods

Product Name:Carbamic acid, [(1R)-2-hydroxy-1-(methoxymethyl)ethyl]-, 1,1-dimethylethyl
CAS Number:183793-49-9
Molecular formula:C9H19NO4
Molecular Weight:205.25

134167-07-0 Synthesis

L-Serine, N-[(1,1-diMethylethoxy)carbonyl]-O-Methyl-, Methyl ester

134167-07-0
33 suppliers
$58.00/100mg

Carbamic acid, [(1R)-2-hydroxy-1-(methoxymethyl)ethyl]-, 1,1-dimethylethyl

183793-49-9
26 suppliers
$280.00/1g

Yield:183793-49-9 85%

Reaction Conditions:

with sodium tetrahydridoborate in methanol;lithium hydroxide monohydrate at 0 - 20;

Steps:

(R)-tert-butyl 1-hydroxy-3-methoxypropan-2-ylcarbamate (7)

To a solution of (R)-tert-butyl1-hydroxy-3-methoxypropan-2-ylcarbamate 60.702 g, 3.0 mmolin CH3OH/H2O (1:1, 6 mL)was added NaBH4 (227 mg, 6.0 mmol) in several portions at 0 . The mixture was allowed to warm to room temperature and stirred overnight. Then it was extracted with EtOAc (3 x 5mL) andthe organic layer was washed with brine (5 mL), dried over anhydrous Na2SO4 and concentrated.The residue was purified by flash chromatography on silica gel (ethyl acetate /petroleum ether =1:2) to afford 7 as colorless oil (0.56 g, 85%). [α]D20 = -3.38 (c = 1.0, CHCl3). 1H NMR (400 MHz,CDCl3): δ 5.29 (br s, 1H), 3.75 (d, J = 9.6, 2H), 3.67-3.64 (m, 1H), 3.54 (d, J = 11.6, 2H), 3.36 (s,3H), 2.84 (s, 1H), 1.45 (s, 9H). 13C NMR (100 MHz, CDCl3): δ 156.0, 79.5, 72.4, 62.9, 59.0, 51.4,28.3. HRMS (ESI): calcd. for C9H19NO4Na [M+Na]+ 228.1206; found 228.1216.

References:

Gao, Ya-Ru;Guo, Shi-Huan;Zhang, Zhuan-Xiang;Mao, Shuai;Zhang, Yan-Lei;Wang, Yong-Qiang [Tetrahedron Letters,2013,vol. 54,# 48,p. 6511 - 6513] Location in patent:supporting information

51293-47-1 Synthesis