| Identification | Back Directory | [Name]
TERT-BUTYL TRANS-(4-HYDROXYMETHYL)CYCLOHEXYLCARBAMATE | [CAS]
239074-29-4 | [Synonyms]
tert-Butyl (trans-4-(hydroxymethyl)
trans-4-(Boc-amino)cyclohexanemethanol
trans-1-(Boc-amino)-4-(hydroxymethyl)cyclohexane,97%
trans-1-(Boc-aMino)-4-(hydroxyMethyl)cyclohexane, 97%
TERT-BUTYL TRANS-(4-HYDROXYMETHYL)CYCLOHEXYLCARBAMATE
Trans tert-butyl 4-(hydroxyMethyl)cyclohexyl)carbaMate
trans-4-(tert-Butoxycarbonylamino)cyclohexane-1-methanol
tert-butyl ((1r,4r)-4-(hydroxymethyl)cyclohexyl)carbamate
tert-butyl N-[trans-4-(hydroxymethyl)cyclohexyl]carbamate
tert-Butyl trans-4-(hydroxymethyl)cyclohexylcarbamate FP160825
(trans-4-Hydroxymethylcyclohexyl)carbamic acid tert-butyl ester
trans-N-[4-(Hydroxymethyl)cyclohexyl]carbamic acid tert-butyl ester
carbamic acid, n-[trans-4-(hydroxymethyl)cyclohexyl]-, 1,1-dimethylethyl ester | [Molecular Formula]
C12H23NO3 | [MDL Number]
MFCD03844605 | [MOL File]
239074-29-4.mol | [Molecular Weight]
229.32 |
| Chemical Properties | Back Directory | [Boiling point ]
351.6±11.0 °C(Predicted) | [density ]
1.05±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
Slightly Soluble (4.4 g/L) (25°C). | [form ]
Solid | [pka]
12.50±0.40(Predicted) | [Appearance]
White to off-white Solid | [InChI]
InChI=1S/C12H23NO3/c1-12(2,3)16-11(15)13-10-6-4-9(8-14)5-7-10/h9-10,14H,4-8H2,1-3H3,(H,13,15)/t9-,10- | [InChIKey]
SGNKPJPMWHKOJO-MGCOHNPYSA-N | [SMILES]
C(OC(C)(C)C)(=O)N[C@@H]1CC[C@@H](CO)CC1 |
| Hazard Information | Back Directory | [Uses]
trans-1-(Boc-amino)-4-(hydroxymethyl)cyclohexane is used to prepare C-2 hydroxyethyl imidazopyrrolo pyridines as JAK1 inhibitors. It is also used to prepare Mer kinase inhibitors for treatment of pediatric acute lymphoblastic leukemia. | [Synthesis]
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. | [References]
[1] Patent: WO2018/67422, 2018, A1. Location in patent: Page/Page column 44; 45
[2] Patent: WO2018/69863, 2018, A1. Location in patent: Page/Page column 121-122
[3] Patent: EP2017261, 2009, A1. Location in patent: Page/Page column 30-31
[4] Patent: US2010/273841, 2010, A1. Location in patent: Page/Page column 22
[5] Patent: WO2011/92293, 2011, A2. Location in patent: Page/Page column 99-100 |
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