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Conditions | Yield |
---|---|
Stage #1: 2,2-dimethyl-3-hydroxypropionaldehyde With sodium hydroxide at 85 - 95℃; for 2h; Stage #2: With ammonium hydroxide; H1044 at 60℃; for 8h; pH=7 - 9; | 91% |
With phosphotungstic acid; dihydrogen peroxide In water at 55℃; for 2h; Temperature; Reagent/catalyst; Time; | 85% |
With sodium hydroxide; oxygen; palladium/alumina at 39.85℃; under 760 Torr; Kinetics; Further Variations:; Temperatures; | |
Multi-step reaction with 2 steps 1: water; aluminium amalgam 2: potassium permanganate View Scheme |
N-[3-acetoxy-2,2-dimethylpropanoyl]-S-methyl-S-2-pyridylsulfoximine
A
3-Hydroxy-2,2-dimethylpropanoic acid
B
imino(methyl)(pyridin-2-yl)-λ6-sulfanone
Conditions | Yield |
---|---|
With hydrogenchloride; water at 50℃; for 3h; | A 88% B 87% |
Methyl 2,2-dimethyl-3-hydroxypropionate
3-Hydroxy-2,2-dimethylpropanoic acid
Conditions | Yield |
---|---|
With water; lithium hydroxide In tetrahydrofuran; methanol at 0 - 20℃; for 1.5h; | 73% |
With lithium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 1.3h; | |
With lithium hydroxide In tetrahydrofuran; methanol; water at 0 - 20℃; |
3-Hydroxy-2,2-dimethylpropanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride; water for 12h; Inert atmosphere; Schlenk technique; Reflux; | 56% |
Conditions | Yield |
---|---|
Stage #1: formaldehyd; L-valine With ketopantoate hydroxymethyltransferase; nickel dichloride at 20℃; for 24h; pH=7.5; Enzymatic reaction; Stage #2: With dihydrogen peroxide pH=7.5; Stage #3: With catalase from bovine liver In aq. phosphate buffer pH=7; Enzymatic reaction; | 51% |
carbon monoxide
3-hydroxy-2-methyl-1-propene
A
dihydro-4-methyl-2(3H)-furanone
B
3-Hydroxy-2,2-dimethylpropanoic acid
Conditions | Yield |
---|---|
Stage #1: carbon monoxide; 3-hydroxy-2-methyl-1-propene With dicarbonylacetylacetonato rhodium (I); 2-isopropoxy-1-methyl-3-phenyl-2,3-dihydro-1H-benzo[d][1,3]azaphosphole; hydrogen; toluene-4-sulfonic acid In benzene at 45℃; under 20686.5 Torr; for 12h; Stage #2: With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene In water; tert-butyl alcohol at 20℃; regioselective reaction; | A n/a B 49% |
2,2-dimethyl-3-hydroxypropionaldehyde
A
3-Hydroxy-2,2-dimethylpropanoic acid
B
2,2-Dimethyl-1,3-propanediol
Conditions | Yield |
---|---|
With potassium carbonate | |
With potassium carbonate |
3-hydroxy-2,2-dimethylpropionitrile
3-Hydroxy-2,2-dimethylpropanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride |
3-acetoxy-2,2-dimethyl-propionitrile
3-Hydroxy-2,2-dimethylpropanoic acid
Conditions | Yield |
---|---|
Verseifung; |
2,2-dimethyl-3-pivaloyloxy-propionic acid
3-Hydroxy-2,2-dimethylpropanoic acid
Conditions | Yield |
---|---|
Hydrolysis; |
Conditions | Yield |
---|---|
With potassium permanganate | |
With sodium hydroxide; potassium permanganate | |
With potassium permanganate | |
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid 3: sodium hydroxide / methanol View Scheme |
4-chloro-3,3-dimethylbutane-2-one
3-Hydroxy-2,2-dimethylpropanoic acid
2-Carboxyl-2,2-dimethyl ethyl radical
3-Hydroxy-2,2-dimethylpropanoic acid
Conditions | Yield |
---|---|
With hydroxide In water at 20 - 24℃; Rate constant; at various pH; |
Trimethylacetic acid
A
3-Hydroxy-2,2-dimethylpropanoic acid
B
2,2,5,5-tetramethylhexanedioic acid
Conditions | Yield |
---|---|
das Natrium-Salz reagiert;beim Leiten durch eine Methan-Sauerstoff-Flamme; |
3-hydroxy-2,2-dimethylpropionitrile
3-Hydroxy-2,2-dimethylpropanoic acid
(hydroxy-lin-pentakis-pivaloyloxy)-pivalic acid
3-Hydroxy-2,2-dimethylpropanoic acid
Conditions | Yield |
---|---|
With zinc; benzene Verseifen des entstehenden Aethylesters mit Kalilauge; |
2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate
A
3-Hydroxy-2,2-dimethylpropanoic acid
B
2,2-Dimethyl-1,3-propanediol
3-hydroxy-2,2-dimethylpropionaldoxime
3-Hydroxy-2,2-dimethylpropanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Destillation 2: hydrochloric acid View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: bromine / 150 °C 2: Hydrolysis View Scheme |
3-chloropivalic acid
3-Hydroxy-2,2-dimethylpropanoic acid
Conditions | Yield |
---|---|
With sodium hydroxide In water |
methanol
2,2-Dimethyl-1,3-propanediol
A
3-Hydroxy-2,2-dimethylpropanoic acid
B
Methyl 2,2-dimethyl-3-hydroxypropionate
Conditions | Yield |
---|---|
With 1% Pd/TiO2; oxygen; sodium hydroxide at 80℃; under 2250.23 Torr; for 24h; | |
With 1 wt% Au/TiO2; oxygen; sodium hydroxide at 80℃; under 2250.23 Torr; Solvent; |
methanol
2,2-Dimethyl-1,3-propanediol
A
2,2-dimethyl-3-hydroxypropionaldehyde
B
3-Hydroxy-2,2-dimethylpropanoic acid
C
Methyl 2,2-dimethyl-3-hydroxypropionate
Conditions | Yield |
---|---|
With 1% Au-Pd/TiO2; oxygen; sodium hydroxide at 80℃; under 2250.23 Torr; for 4h; |
(3-hydroxy-2,2-dimethyl-propyl)acetate
3-Hydroxy-2,2-dimethylpropanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: sodium hydroxide / methanol View Scheme |
Conditions | Yield |
---|---|
With sodium hydroxide In methanol |
Conditions | Yield |
---|---|
With aluminum oxide; bismuth(III) oxide; sodium hydroxide In water at 70℃; for 2h; Temperature; |
3-Hydroxy-2,2-dimethylpropanoic acid
Conditions | Yield |
---|---|
With tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; oxygen In acetone at -5℃; for 20h; Glovebox; | 8 mg |
3-Hydroxy-2,2-dimethylpropanoic acid
tert-butyldimethylsilyl chloride
3-((tert-butyldimethylsilyl)oxy)-2,2-dimethylpropanoic acid
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane | 100% |
With 1H-imidazole In tetrahydrofuran |
3-Hydroxy-2,2-dimethylpropanoic acid
benzyl bromide
benzyl 2,2-dimethyl-3-hydroxypropanoic acid
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 16h; | 100% |
Stage #1: 3-Hydroxy-2,2-dimethylpropanoic acid With caesium carbonate In methanol; water Stage #2: benzyl bromide In N,N-dimethyl-formamide for 7h; Further stages.; | 5.64 g |
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 5h; |
3-Hydroxy-2,2-dimethylpropanoic acid
1-Chloroethyl ethyl carbonate
rac-1-ethoxycarbonyloxy-ethyl 3-hydroxy-2,2-dimethylpropanoate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 70℃; | 100% |
3-Hydroxy-2,2-dimethylpropanoic acid
Conditions | Yield |
---|---|
Stage #1: 3-Hydroxy-2,2-dimethylpropanoic acid With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 4-bromodeacetyl colchicine In N,N-dimethyl-formamide at 20℃; | 100% |
3-phenyl-propionaldehyde
3-Hydroxy-2,2-dimethylpropanoic acid
5,5-dimethyl-2-(2-phenylethyl)-1,3-dioxan-4-one
Conditions | Yield |
---|---|
Stage #1: 3-Hydroxy-2,2-dimethylpropanoic acid With 1,1,1,3,3,3-hexamethyl-disilazane In dichloromethane for 12h; Stage #2: 3-phenyl-propionaldehyde With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 2h; Further stages.; | 99% |
3-Hydroxy-2,2-dimethylpropanoic acid
acetyl chloride
3-acetoxy-2,2-dimethylpropionic acid
Conditions | Yield |
---|---|
Heating; | 97% |
at 0 - 20℃; for 16h; Inert atmosphere; | 96% |
With pyridine at 0 - 20℃; for 3h; | 95% |
3-Hydroxy-2,2-dimethylpropanoic acid
2-benzyl-3-(dimethylamino)-2-methyl-2H-azirine
3-hydroxy-2,2-dimethyl-N-[1-methyl-1-(N,N-dimethylcarbamoyl)-2-phenylethyl]propanamide
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 30h; Addition; | 97% |
In tetrahydrofuran at 20℃; for 24h; | 88% |
3-Hydroxy-2,2-dimethylpropanoic acid
O-benzylethanolamine
N-(2-(benzyloxy)ethyl)-3-hydroxy-2,2-dimethylpropanamide
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere; | 97% |
With benzotriazol-1-ol In dichloromethane | 97% |
3,4-dihydro-2H-pyran
3-Hydroxy-2,2-dimethylpropanoic acid
2,2-dimethyl-3-(tetrahydropyran-2-yloxy)-propionic acid
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 3h; | 95% |
3-Hydroxy-2,2-dimethylpropanoic acid
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; | 94% |
3-Hydroxy-2,2-dimethylpropanoic acid
2,2-dimethyl-3-(N-methyl-N-phenylamino)-2H-azirine
3-hydroxy-2,2-dimethyl-N-[1-methyl-1-(N-methyl-N-phenylcarbamoyl)ethyl]propanamide
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 17h; | 93% |
In tetrahydrofuran at 20℃; for 24h; | 93% |
2,3,4-tri-O-acetyl-L-rhamnopyranosyl ortho-hexynylbenzoate
3-Hydroxy-2,2-dimethylpropanoic acid
C17H26O10
Conditions | Yield |
---|---|
With trifluoromethanesulfonyloxy(triphenylphosphine)gold(I); boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; Molecular sieve; Inert atmosphere; chemoselective reaction; | 92% |
3-Hydroxy-2,2-dimethylpropanoic acid
7-methoxyspiro[chroman-2,4'-piperidin]-4-one hydrochloric acid
Conditions | Yield |
---|---|
Stage #1: 3-Hydroxy-2,2-dimethylpropanoic acid With HATU In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: 7-methoxyspiro[chroman-2,4'-piperidin]-4-one hydrochloric acid With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h; | 92% |
3-Hydroxy-2,2-dimethylpropanoic acid
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 12h; Temperature; Reagent/catalyst; Solvent; | 89.6% |
3-Hydroxy-2,2-dimethylpropanoic acid
L-phenylalanine tert-butyl ester hydrochloride
tert-butyl (S)-2-[(3-hydroxy-2,2-dimethylpropanoyl)amino]-3-phenylpropanoate
Conditions | Yield |
---|---|
With triethylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one In tetrahydrofuran at 20℃; | 89% |
Conditions | Yield |
---|---|
In chloroform a soln. of ligand added dropwise to a soln. of Ti complex, stirred for 15 min; evapd. (vac.), suspended in hexanes, filtered, vac.-dried overnight; elem. anal.; | A 89% B n/a |
aminomalonic acid diethyl ester
3-Hydroxy-2,2-dimethylpropanoic acid
diethyl-N-(β-hydroxypivaloyl)-aminomalonate
Conditions | Yield |
---|---|
With 1-cyclohexyl-3-(2-morpholino-ethyl)-carbodiimide; benzotriazol-1-ol; triethylamine In dichloromethane for 20h; | 88% |
3-Hydroxy-2,2-dimethylpropanoic acid
allyl bromide
2-propenyl 2,2-dimethyl-3-hydroxypropanoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 18h; | 88% |
aminomalonic acid diethyl ester
3-Hydroxy-2,2-dimethylpropanoic acid
A
diethyl-N-(β-hydroxypivaloyl)-aminomalonate
B
N-[Di-(ethoxycarbonyl)methyl]-3,3-dimethyl-2-azetidinone
Conditions | Yield |
---|---|
A 88% B n/a |
2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate
3-Hydroxy-2,2-dimethylpropanoic acid
C39H36O12
Conditions | Yield |
---|---|
With trifluoromethanesulfonyloxy(triphenylphosphine)gold(I); boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; Molecular sieve; Inert atmosphere; chemoselective reaction; | 88% |
Conditions | Yield |
---|---|
With pyridine at 60℃; for 8h; Inert atmosphere; Sealed tube; | 88% |
3-Hydroxy-2,2-dimethylpropanoic acid
N-benzyloxyamine
O-benzyl-2,2-dimethyl-3-hydroxypropano hydroxamate
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water pH 4-5; | 87% |
With diisopropyl-carbodiimide In tetrahydrofuran |
3-Hydroxy-2,2-dimethylpropanoic acid
Conditions | Yield |
---|---|
Stage #1: 3-Hydroxy-2,2-dimethylpropanoic acid With HATU In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: N-(6-(5,5-dimethyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-3- yl)pyridin-2-yl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-7-carboxamide hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h; | 87% |
3-Hydroxy-2,2-dimethylpropanoic acid
methyl (2S)-2-amino-3-phenylpropanoate hydrochloride
Conditions | Yield |
---|---|
With triethylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one In tetrahydrofuran at 20℃; | 86% |
3-Hydroxy-2,2-dimethylpropanoic acid
2-benzyl-2-methyl-3-(N-methyl-N-phenylamino)-2H-azirine
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 28h; | 84% |
3-Hydroxy-2,2-dimethylpropanoic acid
Conditions | Yield |
---|---|
In chloroform a soln. of ligand added dropwise to a soln. of Ti complex, stirred for 15 min; evapd. (vac.), suspended in hexanes, filtered, vac.-dried overnight; elem. anal.; | 84% |
3-Hydroxy-2,2-dimethylpropanoic acid
2-tert-butoxypyridine
tert-butyl 3-hydroxy-2,2-dimethylpropanoate
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In toluene at 20℃; for 2h; | 84% |
2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate
3-Hydroxy-2,2-dimethylpropanoic acid
C39H36O12
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-pyridine; trifluoromethanesulfonyloxy(triphenylphosphine)gold(I) In dichloromethane at 20℃; Molecular sieve; Inert atmosphere; chemoselective reaction; | 82% |
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