TERT-BUTYL TRANS-(4-HYDROXYMETHYL)CYCLOHEXYLCARBAMATE Chemical Properties

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

TERT-BUTYL TRANS-(4-HYDROXYMETHYL)CYCLOHEXYLCARBAMATE Usage And Synthesis

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

TERT-BUTYL TRANS-(4-HYDROXYMETHYL)CYCLOHEXYLCARBAMATE(239074-29-4)Related Product Information

• tert-butyl (1r,4r)-4-aminocyclohexane-1-carboxylate
• trans-Methyl-4-aMinocyclohexanecarboxylate
• TRANS-4-AMINO-CYCLOHEXANE CARBOXYLIC ACID HYDROCHLORIDE
• (1r,4r)-methyl 4-(hydroxymethyl)cyclohexanecarboxylate
• Methyl trans-4-(tert-butoxycarbonylamino)cyclohexanecarboxylate
• trans-4-Aminocyclohexanemethanol
• BOC-1,4-TRANS-ACHC-OH
• TERT-BUTYL TRANS-(4-HYDROXYMETHYL)CYCLOHEXYLCARBAMATE
• 4-(TERT-BUTOXYCARBONYLAMINO)BICYCLO[2.2.2]OCTANE-1-CARBOXYLIC ACID
• 4-(BOC-AMINO)CYCLOHEXANECARBOXYLIC ACID
• METHYL 4-(TERT-BUTYLCARBONYLAMINO)CUBANECARBOXYLATE
• 4-TERT-BUTOXYCARBONYLAMINO-CUBANE-1-CARBOXYLIC ACID
• 7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-1-carboxylic acid
• BOC-(4-CIS/TRANS)-1, 1-ACCH(4-CH2OH)
• 1, 1-ACCH(4-AMINO-BOC)-OME
• FMOC-1, 1-ACCH(4-AMINO-BOC)
• BOC-CIS-1,4-AMINO-1-CYCLOHEXANE CARBOXYLIC ACID
• 1-BOC-AMINOCYCLOHEXANE-1,4-DICARBOXYLIC ACID