22195-47-7

Basic information

• Product Name: (2,2-DIMETHYL-[1,3]-DIOXOLAN-4-YL)-METHYLAMINE
• Synonyms: 2,2-DIMETHYL-1,3-DIOXOLANE-4-METHANAMINE;(2,2-DIMETHYL-[1,3]-DIOXOLAN-4-YL)-METHYLAMINE;2,2-Dimethyl-1,3-Dioxolane-4-Methanamine97%;2,2-DIMETHYL-1,3-DIOXOLAN-4-METHYLAMINE;(2,2-DiMethyl-[1,3]-dioxolan-4-YL)-MethanaMine;2,2-DiMethyl-1,3-dioxolane-4-MethanaMine 97%;1,3-Dioxolane-4-methanamine, 2,2-dimethyl-
• CAS NO: 22195-47-7
• Molecular Formula: C₆H₁₃NO₂
• Molecular Weight: 131.17
• Product Categories: Heterocyclic Building Blocks;O-Containing;Others;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 22195-47-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 147-148 °C14 mm Hg(lit.)
• Flash Point: 155 °F
• Appearance: Colorless to yellow/Liquid
• Density: 1.012 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.59mmHg at 25°C
• Refractive Index: n20/D 1.438(lit.)
• PKA: 9.16±0.29(Predicted)
• CAS DataBase Reference: (2,2-DIMETHYL-[1,3]-DIOXOLAN-4-YL)-METHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (2,2-DIMETHYL-[1,3]-DIOXOLAN-4-YL)-METHYLAMINE(22195-47-7)
• EPA Substance Registry System: (2,2-DIMETHYL-[1,3]-DIOXOLAN-4-YL)-METHYLAMINE(22195-47-7)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 2735 8/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 22195-47-7(Hazardous Substances Data)

Usage

General Description

(2,2-DIMETHYL-[1,3]-DIOXOLAN-4-YL)-METHYLAMINE, also known as MDMDOH, is a chemical compound with the molecular formula C6H13NO2. It is an organic compound that is commonly used as a reagent in chemical synthesis, particularly in the production of pharmaceuticals and other fine chemicals. MDMDOH is a colorless liquid with a distinctive odor, and it is known for its high reactivity and versatility as a building block in organic synthesis. It is also used in the production of various polymers and as a reagent in the manufacturing of agricultural chemicals. MDMDOH is considered to be a valuable chemical in the field of organic chemistry due to its unique structural and functional properties.

InChI:InChI=1/C6H13NO2/c1-6(2)8-4-5(3-7)9-6/h5H,3-4,7H2,1-2H3

Synthetic route

4-(azidomethyl)-2,2‑dimethyl-1,3-dioxolane (25261-56-7) → 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7)

Conditions	Yield
With sodium sulfide In methanol at 55℃; for 24h;	93%
With hydrazine hydrate In ethanol at 20℃; chemoselective reaction;	90%
With 15% palladium on carbon; hydrogen In methanol at 20℃; for 24h;	83%
With palladium 10% on activated carbon; hydrogen In methanol	5.8 g

2-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-1H-isoindole-1,3(2H)-dione (40137-25-5) → 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7)

Conditions	Yield
With hydrazine hydrate In methanol Heating;	90%

5-chloromethyl-2,2-dimethyl-1,3-dioxolane (4362-40-7) → bis((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)amine (52813-61-3) + 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7)

Conditions	Yield
With ammonia at 140℃;

4-azidomethyl-2,2-dimethyl-[1,3]dioxolane → 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol for 8h; Yield given;

(E,Z)-(R)-2,3-O-isopropylidene-glyceraldoxime (756477-96-0) → 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 5h; Ambient temperature;

(R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8) → 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 20 h / 20 °C 2: 90 percent / hydrazine monohydrate / methanol / Heating View Scheme
Multi-step reaction with 3 steps 1: 96 percent / Et3N / CH2Cl2 / 15 h / Ambient temperature 2: 93 percent / aq. NaN3 / dimethylformamide / 6 h / 110 °C 3: 93 percent / aq. Na2S / methanol / 24 h / 55 °C View Scheme
With ammonia; hydrogen at 200℃; under 90009 Torr; Temperature; Reagent/catalyst;

(R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-butane-1,2,3,4-tetraol → 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. NaIO4 / tetrahydrofuran / 2 h / 0 °C 2: NH2OH*HCl, Et3N / tetrahydrofuran; methanol / 5 h / 10 °C 3: LiAlH4 / tetrahydrofuran / 5 h / Ambient temperature View Scheme
Multi-step reaction with 5 steps 1: aq. NaIO4 / tetrahydrofuran / 2 h / 0 °C 2: NaBH4 / ethyl acetate; ethanol / 2.5 h / Ambient temperature 3: 80.3 percent / pyridine / Ambient temperature 4: NaN3 / dimethylsulfoxide / 1.17 h / 100 °C 5: H2 / 5percent Pd/C / methanol / 8 h View Scheme

Sodium; (R)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,3,4-trihydroxy-butyrate → 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: Pb(OAc)4 / ethyl acetate / 3.5 h / 0 - 20 °C 2: NH2OH*HCl, Et3N / tetrahydrofuran; methanol / 5 h / 10 °C 3: LiAlH4 / tetrahydrofuran / 5 h / Ambient temperature View Scheme
Multi-step reaction with 5 steps 1: Pb(OAc)4 / ethyl acetate / 3.5 h / 0 - 20 °C 2: NaBH4 / ethyl acetate; ethanol / 2.5 h / Ambient temperature 3: 80.3 percent / pyridine / Ambient temperature 4: NaN3 / dimethylsulfoxide / 1.17 h / 100 °C 5: H2 / 5percent Pd/C / methanol / 8 h View Scheme

1,2-O-isopropylidene-D-glycerol (14347-78-5) → 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 80.3 percent / pyridine / Ambient temperature 2: NaN3 / dimethylsulfoxide / 1.17 h / 100 °C 3: H2 / 5percent Pd/C / methanol / 8 h View Scheme

(4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde (22323-80-4) → 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: NH2OH*HCl, Et3N / tetrahydrofuran; methanol / 5 h / 10 °C 2: LiAlH4 / tetrahydrofuran / 5 h / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: NaBH4 / ethyl acetate; ethanol / 2.5 h / Ambient temperature 2: 80.3 percent / pyridine / Ambient temperature 3: NaN3 / dimethylsulfoxide / 1.17 h / 100 °C 4: H2 / 5percent Pd/C / methanol / 8 h View Scheme

5,6-O-isopropylidene-L-ascorbic acid (15042-01-0) → 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: LiAlH4 / tetrahydrofuran / 2 h / Heating 2: aq. NaIO4 / tetrahydrofuran / 2 h / 0 °C 3: NH2OH*HCl, Et3N / tetrahydrofuran; methanol / 5 h / 10 °C 4: LiAlH4 / tetrahydrofuran / 5 h / Ambient temperature View Scheme
Multi-step reaction with 6 steps 1: LiAlH4 / tetrahydrofuran / 2 h / Heating 2: aq. NaIO4 / tetrahydrofuran / 2 h / 0 °C 3: NaBH4 / ethyl acetate; ethanol / 2.5 h / Ambient temperature 4: 80.3 percent / pyridine / Ambient temperature 5: NaN3 / dimethylsulfoxide / 1.17 h / 100 °C 6: H2 / 5percent Pd/C / methanol / 8 h View Scheme
Multi-step reaction with 4 steps 1: NaBH4 / ethanol / 4 h / Ambient temperature 2: Pb(OAc)4 / ethyl acetate / 3.5 h / 0 - 20 °C 3: NH2OH*HCl, Et3N / tetrahydrofuran; methanol / 5 h / 10 °C 4: LiAlH4 / tetrahydrofuran / 5 h / Ambient temperature View Scheme
Multi-step reaction with 6 steps 1: NaBH4 / ethanol / 4 h / Ambient temperature 2: Pb(OAc)4 / ethyl acetate / 3.5 h / 0 - 20 °C 3: NaBH4 / ethyl acetate; ethanol / 2.5 h / Ambient temperature 4: 80.3 percent / pyridine / Ambient temperature 5: NaN3 / dimethylsulfoxide / 1.17 h / 100 °C 6: H2 / 5percent Pd/C / methanol / 8 h View Scheme

(S)-1-O-tosyl-2,3-O-isopropylideneglycerol (23735-43-5) → 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaN3 / dimethylsulfoxide / 1.17 h / 100 °C 2: H2 / 5percent Pd/C / methanol / 8 h View Scheme

(2,2-dimethyl-1,3-dioxolan-4-yl)methyl methanesulfonate (34331-40-3) → 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / aq. NaN3 / dimethylformamide / 6 h / 110 °C 2: 93 percent / aq. Na2S / methanol / 24 h / 55 °C View Scheme
Multi-step reaction with 2 steps 1: sodium azide / N,N-dimethyl-formamide; water / 80 - 90 °C 2: hydrogen; palladium 10% on activated carbon / methanol View Scheme

3-Amino-1,2-propanediol (616-30-8, 13552-31-3) + 2,2-dimethoxy-propane (77-76-9) → 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7)

Conditions	Yield
Stage #1: 3-Amino-1,2-propanediol With hydrogenchloride In water at 20℃; for 0.25h; pH=1; Stage #2: 2,2-dimethoxy-propane With toluene-4-sulfonic acid In water at 85℃; for 0.5h; Stage #3: With sodium hydroxide In water pH=9;

4-iodomethyl-2,2-dimethyl-[1,3]dioxolane → 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium azide / N,N-dimethyl-formamide / 6 h / 60 °C 2: hydrogen; 15% palladium on carbon / methanol / 24 h / 20 °C View Scheme

(R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8) → bis((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)amine (52813-61-3) + 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7)

Conditions	Yield
With ammonia; hydrogen In o-xylene at 180 - 400℃; under 750.075 Torr; for 18h; Temperature; Reagent/catalyst; Autoclave;

2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → rac-(2,2-dimethyl-1,3-dioxolan-4-yl)methanamine hydrochloride

Conditions	Yield
With hydroxylamine hydrochloride In ethanol for 2h; Reflux;	100%

1,1'-carbonyldiimidazole (530-62-1) + 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → N-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-1H-imidazole-1-carboxamide (1207634-75-0)

Conditions	Yield
In dichloromethane at 20℃; for 2h;	99%

methanesulfonyl chloride (124-63-0) + 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)methanesulfonamide

Conditions	Yield
With triethylamine In dichloromethane Cooling with ice;	98%
With pyridine In diethyl ether for 2.5h;	12%
With pyridine In diethyl ether for 2.5h;	12%

2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) + 3-(1H-1-triphenylmethylimidazol-4-yl)propanoic acid (160446-35-5) → N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3-(1-trityl-1H-imidazol-4-yl)propanamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃;	98%

p-toluenesulfonyl chloride (98-59-9) + 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → N-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)(p-toluenesulfonamide)

Conditions	Yield
With triethylamine In dichloromethane Cooling with ice;	97%

carbonic acid dimethyl ester (616-38-6) + 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → methyl (2,2-dimethyl-1,3-dioxolan-4-yl)methylcarbamate

Conditions	Yield
With 2-hydroxypyridin; zirconium(IV) tert-butoxide at 80℃; for 12h;	96%

benzenesulfonyl chloride (98-09-9) + 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → N-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)benzenesulfonamide

Conditions	Yield
With triethylamine In dichloromethane Cooling with ice;	95%

trifluoracetyl chloride (354-32-5) + 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → N-[((+/-)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2,2,2-trifluoroacetamide

Conditions	Yield
With triethylamine In dichloromethane Cooling with ice;	92%

methyl 4-bromo-1-[(4-chlorophenyl)methyl]-2-[3-(trifluoromethoxy)phenoxy]-1H-imidazole-5-carboxylate + 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → 4-bromo-1-[(4-chlorophenyl)methyl]-N-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-[3-(trifluoromethoxy)phenoxy]-1H-imidazole-5-carboxamide

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 16h;	91.37%

ethyl 3-(trimethylsilyl)propynoate (16205-84-8) + 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → 3-trimethylsilanyl-propynoic acid (2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-amide

Conditions	Yield
With zirconium(IV) tert-butoxide; benzotriazol-1-ol In toluene at 60℃; for 12h;	91%

2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) + (E)-3-(1-trityl-1H-imidazol-4-yl)acrylic acid (125872-93-7) → (E)-N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3-(1-trityl-1H-imidazol-4-yl)acrylamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃;	90%

C5H3ClN6O2 + 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → N-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-5-methyl-6-nitrotetrazolo[1,5-a]pyrimidin-7-amine

Conditions	Yield
With triethylamine In acetonitrile for 1h;	89%

2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → 3-Amino-1,2-propanediol (616-30-8, 13552-31-3)

Conditions	Yield
With sulfuric acid In water at 70℃; for 3h; Temperature; Reagent/catalyst;	89%
With sulfuric acid In water at 70℃; for 3h; Reagent/catalyst; Temperature;	89%

3,6-diamino-2,5-pyrazinedicarboxylic acid (203798-34-9) + 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → 3,6-diamino-N2,N5-bis((2,2-dimethyl-1,3-dioxolan-4-yl)methyl) pyrazine-2,5-dicarboxamide (960510-28-5)

Conditions	Yield
With ethylene dichloride hydrochloride; benzotriazol-1-ol; triethylamine In water; N,N-dimethyl-formamide at 20℃; for 16h;	88%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 16h;	88%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water; N,N-dimethyl-formamide at 20℃; for 16h;	88%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 16h;	88%

2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → C6H13NO2*F6P(1-)*H(1+)

Conditions	Yield
With ammonium hexafluorophosphate In toluene for 1h; Reflux;	88%

phosgene (75-44-5) + 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → N,N'-bis<<4-(2,2-dimethyl-1,3-dioxolyl)>methyl>urea (159390-20-2)

Conditions	Yield
With sodium hydrogencarbonate In toluene for 16h; Ambient temperature;	87%

2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → BF4(1-)*C6H13NO2*H(1+)

Conditions	Yield
With ammonium tetrafluroborate In toluene for 1h; Reflux;	87%

2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) + 3-methyl-1-(4-nitrophenyl)uracil-5-carboxamide (620591-04-0) → 1-(2,2-dimethyl[1,3]dioxolan-4-ylmethyl)-3-methyluracil-5-carboxamide (620591-06-2)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃;	86%

7-chloro-2-oxo-1,2-dihydro-[1,6]naphthyridine-3-carboxylic acid methyl ester (1386447-80-8) + 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → 7-[(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-amino]-2-oxo-1,2-dihydro-[1,6]naphthyridine-3-carboxylic acid methyl ester (1386447-81-9)

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 140℃; for 2h; Inert atmosphere;	85.2%

8-chloro-2H-[1,3]dioxolo[4,5-g]quinoline (59134-89-3) + 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → 4-[N-(2,2-dimethyl-[1,3]dioxolan-4-yl)methyl]amino-6,7-methylenedioxyquinoline (529488-60-6)

Conditions	Yield
With potassium phosphate; bis[2-(diphenylphosphino)phenyl] ether; palladium diacetate In 1,4-dioxane at 85℃; for 18h;	85%

di-tert-butyl dicarbonate (24424-99-5) + 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → tert-butyl[((+/-)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl]carbamate (949086-94-6)

Conditions	Yield
With sodium carbonate In 1,4-dioxane at 20℃; for 14h;	83%

1-(3-benzyloxy-6-methyl-pyridin-2-ylmethyl)-2-chloro-4,6-dimethyl-1H-benzoimidazole (856895-39-1) + 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → [1-(3-benzyloxy-6-methyl-pyridin-2-ylmethyl)-4,6-dimethyl-1H-benzoimidazol-2-yl]-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-amine

Conditions	Yield
at 130 - 160℃; for 5h;	81%
at 130 - 160℃; for 5h;	81%

2,4-dibromobutanoyl chloride (82820-87-9) + 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → 3-bromo-1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]pyrrolidin-2-one (864658-45-7)

Conditions	Yield
Stage #1: 2,4-dibromobutanoyl chloride; 4-aminomethyl-2,2-dimethyl[1,3]dioxolane With triethylamine In ISOPROPYLAMIDE at 0 - 20℃; for 2h; Stage #2: With sodium hydride In ISOPROPYLAMIDE for 2h;	80%

ethyl trifluoroacetate, (383-63-1) + 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → N-[((+/-)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2,2,2-trifluoroacetamide

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 20h;	76%

1-(4-nitrophenyl)-5-cyano-3-methyluracil (126080-33-9) + 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → 5-cyano-1-(2,2-dimethyl-[1,3]dioxolane-4-ylmethyl)-3-methyluracil

Conditions	Yield
In N,N-dimethyl-formamide at 20℃;	75%

benzoyl chloride (98-88-4) + 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → N-[((+/-)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl]benzamide

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃;	75%

bis-(p-nitrophenyl) carbonate (5070-13-3) + 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → [N-(2,2-dimethyl-1,3-dioxolane-4-methan)-carbamoyl]-p-nitrophenol

Conditions	Yield
With dmap In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;	75%
With dmap In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;	75%

7-chloro-6-nitro-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one + 2,2-dimethyl-1,3-dioxolane-4-methanamine (22195-47-7) → 7-(2,2-dimethyl-1,3-dioxolanylmethylamino)-6-nitro-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

Conditions	Yield
With triethylamine In acetonitrile at 3 - 5℃; for 1h;	75%

Upstream product

• 40137-25-5 2-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-1H-isoindole-1,3(2H)-dione 
• 15042-01-0 5,6-O-isopropylidene-L-ascorbic acid 
• 23735-43-5 (S)-1-O-tosyl-2,3-O-isopropylideneglycerol 
• 23737-52-2 4-iodomethyl-2,2-dimethyl-[1,3]dioxolane 
• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 
• 616-30-8 3-Amino-1,2-propanediol 
• 77-76-9 2,2-dimethoxy-propane 
• 34331-40-3 (2,2-dimethyl-1,3-dioxolan-4-yl)methyl methanesulfonate 
• 22323-80-4 (4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 
• 14347-78-5 1,2-O-isopropylidene-D-glycerol 
• 756477-96-0 (E,Z)-(R)-2,3-O-isopropylidene-glyceraldoxime 
• 25261-56-7 4-(azidomethyl)-2,2?dimethyl-1,3-dioxolane 
• 4362-40-7 5-chloromethyl-2,2-dimethyl-1,3-dioxolane 

Downstream Products

• 159390-20-2 N,N'-bis<<4-(2,2-dimethyl-1,3-dioxolyl)>methyl>urea 
• 1035216-50-2 N-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzyl)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)methanamine 
• 616-30-8 3-Amino-1,2-propanediol 
• 1632161-76-2 benzyl 4-[[7-(4-benzyloxy-4-oxo-butoxy)-6-[(2,2-dimethyl-1,3-dioxolan-4-yl)methylamino]-2-naphthyl]oxy]butanoate 
• 1426336-48-2 6-(N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)methylsulfonamido)-2-(4-(4-fluorophenoxy)phenyl)pyrimidine-4-carboxamide 
• 1093988-21-6 3-[5-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1,3,4-oxadiazol-2-yl]-N-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]benzamide 
• 1093988-49-8 4-[5-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1,3,4-oxadiazol-2-yl]-N-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]benzamide 
• 1391465-47-6 rac-2-(4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)-N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)ethanamine 
• 1386981-19-6 N-(2-chloro-5-(3-chlorobenzylcarbamoyl)phenyl)-2-((2,2-dimethyl-1,3-dioxolan-4-yl)methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxamide 
• 1280168-02-6 6-chloro-N₄,N₈-bis(3,4-dimethoxybenzyl)-N₂-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)pyrimido-[5,4-d]pyrimidine-2,4,8-triamine 

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PROCESS FOR PREPARING SOLKETAL AMINE VIA DIRECT AMINATION

Disclosed a process for preparing a solketal amine via direct amination. It is possible to obtain solketal amines by very simple procedure with desired characteristics such as simplicity, inexpensiveness, high yield and conversion, as well as low environmental impact.

POLY(PHOSPHOESTERS) FOR DELIVERY OF NUCLEIC ACIDS

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Chemo- and Site-Selective Alkyl and Aryl Azide Reductions with Heterogeneous Nanoparticle Catalysts

Site-selective modification of bioactive natural products is an effective approach to generating new leads for drug discovery. Herein, we show that heterogeneous nanoparticle catalysts enable site-selective monoreduction of polyazide substrates for the generation of aminoglycoside antibiotic derivatives. The nanoparticle catalysts are highly chemoselective for reduction of alkyl and aryl azides under mild conditions and in the presence of a variety of easily reduced functional groups. High regioselectivity for monoazide reduction is shown to favor reduction of the least sterically hindered azide. We hypothesize that the observed selectivity is derived from the greater ability of less-hindered azide groups to interact with the surface of the nanoparticle catalyst. These results are complementary to previous Staudinger reduction methods that report a preference for selective reduction of electronically activated azides.