ChemicalBook CAS DataBase List TERT-BUTYL TRANS-(4-HYDROXYMETHYL)CYCLOHEXYLCARBAMATE

TERT-BUTYL TRANS-(4-HYDROXYMETHYL)CYCLOHEXYLCARBAMATE synthesis

8synthesis methods

Product Name:TERT-BUTYL TRANS-(4-HYDROXYMETHYL)CYCLOHEXYLCARBAMATE
CAS Number:239074-29-4
Molecular formula:C12H23NO3
Molecular Weight:229.32

Methyl trans-4-(tert-butoxycarbonylamino)cyclohexanecarboxylate

146307-51-9

239074-29-4

General procedure for the synthesis of tert-butyl trans-(4-hydroxymethyl)cyclohexylcarbamate from methyl trans-4-(tert-butoxycarbonylamino)cyclohexanecarboxylate: a suspension of LiAlH4 (9.0 g, 0.236 mol, 1.12 eq.) in THF (500 mL) was cooled to 0 °C under ice bath conditions. Subsequently, a solution of methyl trans-4-(tert-butoxycarbonylamino)cyclohexanecarboxylate (54.3 g, 0.21 mol, 1.0 eq.) in THF (200 mL) was slowly added to ensure that the reaction temperature was maintained below 10 °C. After the addition was completed, the reaction mixture was transferred to room temperature and stirred overnight. Upon completion of the reaction, the reaction was carefully quenched with sodium sulfate decahydrate (27 g) at 15 °C to 25 °C. The insoluble material was removed by filtration and the filtrate was concentrated to give tert-butyl trans-(4-hydroxymethyl)cyclohexylcarbamate (43 g, 89% yield) as a white powder.MS-ESI: [M + 1]+: 229.1.

146307-51-9 Synthesis

146307-51-9
108 suppliers
$6.00/100mg

239074-29-4
113 suppliers
$11.00/250mg

Yield:239074-29-4 95%

Reaction Conditions:

with methanol;lithium tetrahydridoborate in diethyl ether; for 0.75 h;

References:

Shen, Yudao;McCorvy, John D.;Martini, Michael L.;Rodriguiz, Ramona M.;Pogorelov, Vladimir M.;Ward, Karen M.;Wetsel, William C.;Liu, Jing;Roth, Bryan L.;Jin, Jian [Journal of Medicinal Chemistry,2019,vol. 62,# 9,p. 4755 - 4771]

24424-99-5 Synthesis