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

storage temp. 

2-8°C

Appearance

White to off-white Solid

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

Synthesis

General procedure for the synthesis of cis-1-(Boc-amino)-4-(hydroxymethyl)cyclohexane from di-tert-butyl dicarbonate and (1r,4r)-4-aminocyclohexanemethanol: Di-tert-butyl dicarbonate (3.04 g, 13.9 mmol) was slowly added to (1r,4r)-4-aminocyclohexanemethanol (1.50 g, 11.6 mmol) in a room temperature tetrahydrofuran (20 mL) in a stirred solution. The reaction mixture was stirred overnight at room temperature. Subsequently, the solvent was removed by rotary evaporation and the residue was partitioned between ethyl acetate and water. The organic phase was separated, washed sequentially with water and saturated saline, dried over anhydrous magnesium sulfate, and the solvent was again removed by rotary evaporation. The resulting residue was treated with hexane and the suspension formed was filtered to give cis-1-(Boc-amino)-4-(hydroxymethyl)cyclohexane as a white solid (2.11 g, 79% yield). The product was detected by low resolution mass spectrometry (LRMS) and showed m/z of 228 (M-H)+.1H NMR (DMSO-d6) δ: 0.84-0.95 (m, 2H), 1.05-1.18 (m, 2H), 1.20-1.29 (m, 2H), 1.40 (s, 9H), 1.71-1.80 (m, 3H), 3.14 (m , 1H), 3.21 (t, 2H), 4.41 (t, 1H), 6.73 (d, 1H).

References

[1] Patent: EP2554544, 2013, A1. Location in patent: Paragraph 0161
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S309-S310,S311
[3] Journal of Labelled Compounds and Radiopharmaceuticals, 1999, vol. 42, # 3, p. 293 - 307
[4] Patent: US2015/31674, 2015, A1. Location in patent: Paragraph 0274

TERT-BUTYL CIS-(4-HYDROXYMETHYL)CYCLOHEXYLCARBAMATE(223131-01-9)Related Product Information

• Cyclohexanecarboxylic acid, 4-(cyclopropylamino)-, ethyl ester, cis-
• Cyclohexaneacetic acid, 4-(4-hydroxyphenyl)-, Methyl ester, cis-
• cis-tert-butyl 3-aMinocyclobutanecarboxylate hydrochloride
• (3R,5S)-3,5-diMethylMorpholine
• cis-tert-butyl 3-hydroxycyclobutanecarboxylate
• cis-3-Methylcyclobutanamine hydrochloride
• BOC-1,4-TRANS-ACHC-OH
• TERT-BUTYL CIS-(4-HYDROXYMETHYL)CYCLOHEXYLCARBAMATE
• 4-TERT-BUTOXYCARBONYLAMINO-CUBANE-1-CARBOXYLIC ACID
• 4-(TERT-BUTOXYCARBONYLAMINO)BICYCLO[2.2.2]OCTANE-1-CARBOXYLIC ACID
• 4-(BOC-AMINO)CYCLOHEXANECARBOXYLIC ACID
• METHYL 4-(TERT-BUTYLCARBONYLAMINO)CUBANECARBOXYLATE
• FMOC-1, 1-ACCH(4-AMINO-BOC)
• 1-BOC-AMINOCYCLOHEXANE-1,4-DICARBOXYLIC ACID
• BOC-TRANS-1,4-AMINO-1-CYCLOHEXANE CARBOXYLIC ACID
• 1, 1-ACCH(4-AMINO-BOC)-OME
• BOC-(4-CIS/TRANS)-1, 1-ACCH(4-CH2OH)