25462-17-3

Basic information

• Product Name: 2-(hydroxymethyl)-2-methylpentyl isopropyl-carbamate
• Synonyms: 2-(hydroxymethyl)-2-methylpentyl isopropyl-carbamate;1-Methylethylcarbamic acid 2-(hydroxymethyl)-2-methylpentyl ester;N-isoproply-2-methyl-2-proply-3-idrossipropyl carbamate;IsopropylcarbaMic acid 2-(hydroxyMethyl)-2-Methylpentyl este;N-(1-Methylethyl)carbamic acid 2-(hydroxymethyl)-2-methylpentyl ester;CarbaMic acid,N-(1-Methylethyl)-, 2-(hydroxyMethyl)-2-Methylpentyl ester;(2RS)-2-(Hydroxymethyl)-2-methylpentyl isopropylcarbamate;Isopropylcarbamic acid 2-(hydroxymethyl)-2-methylpentyl ester
• CAS NO: 25462-17-3
• Molecular Formula: C₁₁H₂₃NO₃
• Molecular Weight: 217.30522
• EINECS: 247-009-8
• Mol File: 25462-17-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 337℃
• Flash Point: 157℃
• Appearance: /
• Density: 0.986
• Vapor Pressure: 7.7E-06mmHg at 25°C
• Refractive Index: 1.4549
• PKA: 12.54±0.46(Predicted)
• CAS DataBase Reference: 2-(hydroxymethyl)-2-methylpentyl isopropyl-carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(hydroxymethyl)-2-methylpentyl isopropyl-carbamate(25462-17-3)
• EPA Substance Registry System: 2-(hydroxymethyl)-2-methylpentyl isopropyl-carbamate(25462-17-3)

Safety Data

• Hazardous Substances Data: 25462-17-3(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

Uses

An intermediate in the synthesis of Carisoprodol.

InChI:InChI=1/C11H23NO3/c1-5-6-11(4,7-13)8-15-10(14)12-9(2)3/h9,13H,5-8H2,1-4H3,(H,12,14)

Synthetic route

2-methyl-2-propyl-1,3-propanediol (78-26-2) + N-isopropylformamide (16741-46-1) → N-Mono-isopropyl-2-methyl-2-n-propylpropane-1,3-diol carbamate (25462-17-3)

Conditions	Yield
With dihydrogen peroxide; dicyclohexyl-carbodiimide at 30℃; for 4h; Temperature; Reagent/catalyst;	82%

3-methyl 3-n-propyl oxetane (13911-97-2) + carbon dioxide (124-38-9) + isopropylamine (75-31-0) → N-Mono-isopropyl-2-methyl-2-n-propylpropane-1,3-diol carbamate (25462-17-3)

Conditions	Yield
With C49H74AlNO4; bis(triphenylphosphoranylidene)ammonium iodide In butanone at 100℃; under 7500.75 Torr; for 80h; Autoclave; Sealed tube; chemoselective reaction;	48%

5-Methyl-5-n-propyl-1,3-dioxan-2-one (7148-50-7) + isopropylamine (75-31-0) → N-Mono-isopropyl-2-methyl-2-n-propylpropane-1,3-diol carbamate (25462-17-3)

2-methyl-2-propyl-1,3-propanediol (78-26-2) → N-Mono-isopropyl-2-methyl-2-n-propylpropane-1,3-diol carbamate (25462-17-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) Na / 1.) toluene, 90 deg C, 30 min, 2.) toluene, 88-110 deg C 2: 5 h / Heating View Scheme
Multi-step reaction with 2 steps 1.1: p-toluenesulfonyl chloride; n-butyllithium 1.2: 0 - 60 °C 2.1: C49H74AlNO4; bis(triphenylphosphoranylidene)ammonium iodide / butanone / 80 h / 100 °C / 7500.75 Torr / Autoclave; Sealed tube View Scheme

5-Methyl-5-n-propyl-1,3-dioxan-2-one (7148-50-7) + isopropylamine hydrochloride (15572-56-2) → N-Mono-isopropyl-2-methyl-2-n-propylpropane-1,3-diol carbamate (25462-17-3)

Conditions	Yield
With triethylamine at 90℃; for 2h;

2-methyl-2-propyl-1,3-propanediol (78-26-2) + Isopropyl isocyanate (1795-48-8) → N-Mono-isopropyl-2-methyl-2-n-propylpropane-1,3-diol carbamate (25462-17-3)

Conditions	Yield
In water; toluene

N-Mono-isopropyl-2-methyl-2-n-propylpropane-1,3-diol carbamate (25462-17-3) + Trichloroacetyl isocyanate (3019-71-4) → carisoprodol (78-44-4)

Conditions	Yield
Stage #1: N-Mono-isopropyl-2-methyl-2-n-propylpropane-1,3-diol carbamate; Trichloroacetyl isocyanate In methanol; dichloromethane at 0 - 25℃; for 4h; Stage #2: With potassium carbonate In methanol; dichloromethane at 25℃; for 4h;	96%

N-Mono-isopropyl-2-methyl-2-n-propylpropane-1,3-diol carbamate (25462-17-3) + sodium isocyanate (917-61-3) → carisoprodol (78-44-4)

Conditions	Yield
With hydrogenchloride In dichloromethane at -2 - 2℃; for 10h;	80%
Stage #1: N-Mono-isopropyl-2-methyl-2-n-propylpropane-1,3-diol carbamate; sodium isocyanate With hydrogenchloride In dichloromethane at 0℃; for 2.5h; Stage #2: With sodium hydrogencarbonate In dichloromethane pH=8;

phosgene (75-44-5) + N-Mono-isopropyl-2-methyl-2-n-propylpropane-1,3-diol carbamate (25462-17-3) → carisoprodol (78-44-4)

Conditions	Yield
(i) PhNMe2, (ii) NH3; Multistep reaction;

thiophosgene (463-71-8) + N-Mono-isopropyl-2-methyl-2-n-propylpropane-1,3-diol carbamate (25462-17-3) → N-Isopropyl-<2-methyl-2-propyl-3-thiocarbamoyloxy-propyl>-carbamat (1444-06-0)

Conditions	Yield
(i) antipyrine, (ii) aq. NH3; Multistep reaction;

phosgene (75-44-5) + N-Mono-isopropyl-2-methyl-2-n-propylpropane-1,3-diol carbamate (25462-17-3) + dimethyl amine (124-40-3) → N,N-Dimethyl-N'-isopropyl-2-methyl-2-propyl-propandiol-(1.3)-dicarbamat (92326-71-1)

Conditions	Yield
(i) PhNMe2, (ii) /BRN= 605257/; Multistep reaction;

phosgene (75-44-5) + N-Mono-isopropyl-2-methyl-2-n-propylpropane-1,3-diol carbamate (25462-17-3) + methylamine (74-89-5) → N-Methyl-N'-isopropyl-2-methyl-2-propyl-propandiol-(1.3)-dicarbamat (92168-78-0)

Conditions	Yield
(i) PhNMe2, (ii) /BRN= 741851/; Multistep reaction;

Upstream product

• 13911-97-2 3-methyl 3-n-propyl oxetane 
• 124-38-9 carbon dioxide 
• 75-31-0 isopropylamine 
• 78-26-2 2-methyl-2-propyl-1,3-propanediol 
• 16741-46-1 N-isopropylformamide 
• 1795-48-8 Isopropyl isocyanate 
• 7148-50-7 5-Methyl-5-n-propyl-1,3-dioxan-2-one 
• 15572-56-2 isopropylamine hydrochloride 

Downstream Products

• 78-44-4 carisoprodol 
• 1444-06-0 N-Isopropyl-<2-methyl-2-propyl-3-thiocarbamoyloxy-propyl>-carbamat 

Relevant articles and documents

Catalytic One-Pot Oxetane to Carbamate Conversions: Formal Synthesis of Drug Relevant Molecules

Oxetanes are versatile building blocks in drug-related synthesis to induce property-modulating effects. Whereas related oxiranes are widely used in coupling chemistry with carbon dioxide (CO2) to afford value-added commodity chemicals, oxetane/CO2couplings remain extremely limited despite the recent advances in the synthesis of these four-membered heterocycles. Here we report an effective one-pot three-component reaction (3CR) strategy for the coupling of (substituted) oxetanes, amines and CO2to afford a variety of functionalized carbamates with excellent chemoselectivity and good yields. The process is mediated by an aluminium-based catalyst under relatively mild conditions and the developed catalytic methodology can be applied to the formal synthesis of two pharmaceutically relevant carbamates with the 3CR being a key step. (Figure presented.).

Meprobamate immunoassay

Carisoprodol is a centrally-acting prescription drug of known abuse. Upon ingestion it is rapidly metabolised to meprobamate, also a prescription drug with abuse potential. Current immunoassays are specific for carisoprodol and therefore have a short window of detection and, furthermore, are ineffective at detecting meprobamate. The current invention, underpinned by an antibody specific for meprobamate, overcomes these deficiencies.

PREPARATION OF CARBAMATES

-