trans-4-Hydroxy-D-proline supplier

Name
trans-4-Hydroxy-D-proline
EINECS 219-963-5
CAS No. 3398-22-9
Article Data9
CAS DataBase
Density 1.395 g/cm³
Solubility
Melting Point 260°C
Formula C₅H₉NO₃
Boiling Point 355.2 °C at 760 mmHg
Molecular Weight 131.131
Flash Point 168.6 °C
Transport Information
Appearance White crystal or crystalline powder
Safety 24/25-36/37-26
Risk Codes 22-36/37/38-43
Molecular Structure
Hazard Symbols Xn
Synonyms D-Proline,4-hydroxy-, trans-;(2R,4S)-(+)-4-Hydroxy-D-proline;4-(S)-Hydroxypyrrolidine-2-(R)-carboxylic acid;D-Hydroxyproline;D-trans-4-Hydroxyproline;NSC 206273;trans-4-Hydroxy-D-proline;
PSA 69.56000
LogP -0.87740

Synthetic route

: (2R,4S)-4-(benzyloxy)-1-N-tosylpyrrolidine-2-carboxylic acid

: 3398-22-9
trans-4-hydroxyproline

Conditions

Conditions	Yield
With ammonia; sodium at -70℃; for 3.5h; Inert atmosphere;	79%

: 77449-96-8
N-Acetyl-allo-4-(p-toluenesulfonyloxy)-D-proline

: 3398-22-9
trans-4-hydroxyproline

Conditions

Conditions	Yield
With sodium hydroxide Erhitzen des Reaktionsprodukts mit wss. HCl;

: 114673-33-5
trans-1-(3,5-dinitro-benzoyl)-4-hydroxy-D-proline

: 3398-22-9
trans-4-hydroxyproline

Conditions

Conditions	Yield
With hydrogenchloride
With hydrogenchloride

1-anilinoformyl-d-a-<4-oxy-proline >: 1-anilinoformyl-d-a-<4-oxy-proline >

: 3398-22-9
trans-4-hydroxyproline

Conditions

Conditions	Yield
With ammonia at 95 - 100℃;

: 77449-96-8
N-Acetyl-allo-4-(p-toluenesulfonyloxy)-D-proline

aqueous NaOH: aqueous NaOH

: 3398-22-9
trans-4-hydroxyproline

Conditions

Conditions	Yield
anschliessend Erhitzen mit wss. HCl;

: 618-28-0
trans-4-hydroxy-D,L-proline

: 3398-22-9
trans-4-hydroxyproline

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: aqueous NaOH 2: (1S,2S)-2-amino-1-<4-nitro-phenyl>-propane-1,3-diol 3: aqueous HCl View Scheme
Multi-step reaction with 3 steps 1: sodium hydroxide 2: (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol 3: hydrogenchloride View Scheme

: 77449-95-7
N-Acetyl-allo-4-(p-toluenesulfonyloxy)-D-proline Methyl Ester

: 3398-22-9
trans-4-hydroxyproline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous methanol. NaOH 2: aqueous NaOH / Erhitzen des Reaktionsprodukts mit wss. HCl View Scheme

: 103078-90-6, 114673-32-4, 114673-33-5
trans-1-(3,5-dinitro-benzoyl)-4-hydroxy-DL-proline

: 3398-22-9
trans-4-hydroxyproline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: brucine 2: aqueous HCl View Scheme
Multi-step reaction with 2 steps 1: (1S,2S)-2-amino-1-<4-nitro-phenyl>-propane-1,3-diol 2: aqueous HCl View Scheme
Multi-step reaction with 2 steps 1: (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol 2: hydrogenchloride View Scheme

: 618-28-0
trans-4-hydroxy-D,L-proline

A: 3398-22-9
trans-4-hydroxyproline

B: 51-35-4
4R-4-hydroxyproline

Conditions

Conditions	Yield
With shaking calcined L-Pro chiral ordered mesoporous silica Resolution of racemate;

: (3S,5R)-3-(benzyloxy)-2-hydroxy-5-(hydroxymethyl)-1-N-tosylpyrrolidine

: 3398-22-9
trans-4-hydroxyproline

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 3 h / 0 - 30 °C / Inert atmosphere 2: Jones reagent / acetone / 4 h / 0 °C / Inert atmosphere 3: ammonia; sodium / 3.5 h / -70 °C / Inert atmosphere View Scheme

: 4-O-benzyl-2,3-dideoxy-2-(p-toluenesulfonamido)-D-glucitol

: 3398-22-9
trans-4-hydroxyproline

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium periodate; sodium hydrogencarbonate / water; dichloromethane / 12 h / 0 - 30 °C / Inert atmosphere 2: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 3 h / 0 - 30 °C / Inert atmosphere 3: Jones reagent / acetone / 4 h / 0 °C / Inert atmosphere 4: ammonia; sodium / 3.5 h / -70 °C / Inert atmosphere View Scheme

: 1,6-di-O-acetyl-4-O-benzyl-2,3-dideoxy-2-(p-toluenesulfonamido)-D-glucopyranose

: 3398-22-9
trans-4-hydroxyproline

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 10 h / Reflux; Inert atmosphere 2: sodium periodate; sodium hydrogencarbonate / water; dichloromethane / 12 h / 0 - 30 °C / Inert atmosphere 3: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 3 h / 0 - 30 °C / Inert atmosphere 4: Jones reagent / acetone / 4 h / 0 °C / Inert atmosphere 5: ammonia; sodium / 3.5 h / -70 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 5 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 10 h / Reflux; Inert atmosphere
2: sodium periodate; sodium hydrogencarbonate / water; dichloromethane / 12 h / 0 - 30 °C / Inert atmosphere
3: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 3 h / 0 - 30 °C / Inert atmosphere
4: Jones reagent / acetone / 4 h / 0 °C / Inert atmosphere
5: ammonia; sodium / 3.5 h / -70 °C / Inert atmosphere
View Scheme

: 501-53-1
benzyl chloroformate

: 3398-22-9
trans-4-hydroxyproline

: 155153-78-9
(4S)-1-[(benzyloxy)carbonyl]-4-hydroxy-D-proline

Conditions

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; water at 0℃; for 1h;	100%
Stage #1: benzyl chloroformate; trans-4-hydroxyproline With sodium hydrogencarbonate In water; toluene at 20℃; for 16.25h; Stage #2: With hydrogenchloride In diethyl ether; water pH=2;	93%
Stage #1: benzyl chloroformate; trans-4-hydroxyproline With sodium hydrogencarbonate In water; toluene at 20℃; for 16h; Stage #2: With hydrogenchloride In water pH=2; Cooling with ice;	93%
With sodium hydrogencarbonate
With sodium hydrogencarbonate In water

: 24424-99-5
di-tert-butyl dicarbonate

: 3398-22-9
trans-4-hydroxyproline

: 147266-92-0
(2R,4S )-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane; water at 0 - 20℃;	100%
With sodium hydroxide In 1,4-dioxane; water
With triethylamine In methanol for 2h; Reflux;	11 g

: C8H3ClF5N

: 3398-22-9
trans-4-hydroxyproline

: (2R,4S)-N-(2,4-difluorophenyl)-4-hydroxy-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxamide

Conditions

Conditions	Yield
With titanium(IV) oxide; sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 8h; Inert atmosphere;	93%

: N-(2,5-difluorophenyl)-2,2,2-trifluoroacetimidoyl chloride

: 3398-22-9
trans-4-hydroxyproline

: (2R,4S)-N-(2,5-difluorophenyl)-4-hydroxy-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxamide

Conditions

Conditions	Yield
With titanium(IV) oxide; sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 8h; Inert atmosphere;	92%
With sodium hydrogencarbonate; titanium(IV) oxide

: 3398-22-9
trans-4-hydroxyproline

: 100-51-6
benzyl alcohol

: (2R,4S)-4-hydroxyproline benzyl ester

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene at 125℃; for 20h; Dean-Stark;	91.1%

: 63930-17-6
1,2-di(m-tolyl)disulfane

: 3398-22-9
trans-4-hydroxyproline

: (2S,4R)-2-carboxy-4-(3-fluorophenylthio)pyrrolidine

Conditions

Conditions	Yield
With tributylphosphine In tetrahydrofuran at 60 - 65℃; for 25h; Concentration;	89.7%

: 3398-22-9
trans-4-hydroxyproline

: 481704-21-6
(2R,4S)-methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride

Conditions

Conditions	Yield
With acetyl chloride In methanol; diethyl ether at 20℃;	87.6%

: 1453185-82-4
C8H3BrCl2F3N

: 3398-22-9
trans-4-hydroxyproline

: (2R,4S)-N-(2-bromo-4-chlorophenyl)-4-hydroxy-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxamide

Conditions

Conditions	Yield
With titanium(IV) oxide; sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 8h; Inert atmosphere;	87%

: 143681-32-7
N-(4-chlorophenyl)-2,2,2-trifluoroethanimidoyl chloride

: 3398-22-9
trans-4-hydroxyproline

: (2R,4S)-N-(4-chlorophenyl)-4-hydroxy-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxamide

Conditions

Conditions	Yield
With titanium(IV) oxide; sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 8h; Inert atmosphere;	83%

: 110-16-7
maleic acid

: 3398-22-9
trans-4-hydroxyproline

: 1092655-33-8
(S)-pyrrolidin-3-ol hydrogen maleate

Conditions

Conditions	Yield
Stage #1: trans-4-hydroxyproline With cyclohexenone In cyclohexanol for 3h; Reflux; Stage #2: maleic acid at 35℃; for 0.5h;	80%
Stage #1: trans-4-hydroxyproline With cyclohexenone In cyclohexanol for 3h; Reflux; Stage #2: maleic acid In cyclohexanol at 35℃; for 0.5h;	80%

: 61984-67-6
2,2,2-trifluoro-N-[2-(trifluoromethyl)phenyl]ethanimidoyl chloride

: 3398-22-9
trans-4-hydroxyproline

: (2R,4S)-4-hydroxy-1-(2,2,2-trifluoroacetyl)-N-(2-(trifluoromethyl)phenyl)pyrrolidine-2-carboxamide

Conditions

Conditions	Yield
With titanium(IV) oxide; sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 8h; Reagent/catalyst; Solvent; Time; Inert atmosphere;	78%

: 69563-07-1
2,2,2-trifluoro-N-(3-(trifluoromethyl)phenyl)acetimidoyl chloride

: 3398-22-9
trans-4-hydroxyproline

: (2R,4S)-4-hydroxy-1-(2,2,2-trifluoroacetyl)-N-(3-(trifluoromethyl)phenyl)pyrrolidine-2-carboxamide

Conditions

Conditions	Yield
With titanium(IV) oxide; sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 8h; Inert atmosphere;	77%

: C8H3ClF4N2O2

: 3398-22-9
trans-4-hydroxyproline

: (2R,4S)-N-(4-fluoro-3-nitrophenyl)-4-hydroxy-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxamide

Conditions

Conditions	Yield
With titanium(IV) oxide; sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 8h; Inert atmosphere;	77%

: 145372-31-2
N-(4-nitrophenyl)-2,2,2-trifluoroacetimidoyl chloride

: 3398-22-9
trans-4-hydroxyproline

: (2R,4S)-4-hydroxy-N-(4-nitrophenyl)-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxamide

Conditions

Conditions	Yield
With titanium(IV) oxide; sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 8h; Inert atmosphere;	73%

: 3398-22-9
trans-4-hydroxyproline

: 100243-39-8
3-hydroxypyrrolidine

Conditions

Conditions	Yield
With cyclohexenone; cyclohexanol for 2h; Heating;	70%

: N-(3,5-bis(trifluoromethyl)phenyl)-2,2,2-trifluoroacetimidoyl chloride

: 3398-22-9
trans-4-hydroxyproline

: (2R,4S)-N-(3,5-bis(trifluoromethyl)phenyl)-4-hydroxy-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxamide

Conditions

Conditions	Yield
With titanium(IV) oxide; sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 8h; Inert atmosphere;	70%

: C8H3Cl2F4N

: 3398-22-9
trans-4-hydroxyproline

: (2R,4S)-N-(3-chloro-4-fluorophenyl)-4-hydroxy-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxamide

Conditions

Conditions	Yield
With titanium(IV) oxide; sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 8h; Inert atmosphere;	70%

: 50-00-0
formaldehyd

: 3398-22-9
trans-4-hydroxyproline

: 1451370-71-0
C12H21N2O8P

Conditions

Conditions	Yield
Stage #1: trans-4-hydroxyproline With hydrogenchloride; hypophosphorous acid In water at 20℃; for 1h; Stage #2: formaldehyd In water at 20℃; for 24h;	28%

: 74204-03-8
2-bromo-4-methylvaleryl bromide

: 3398-22-9
trans-4-hydroxyproline

: 1-(DL-α-bromo-isocaproyl)-4-oxy-L-proline

Conditions

Conditions	Yield
With sodium hydroxide

: 590-28-3
potassium cyanate

: 3398-22-9
trans-4-hydroxyproline

: 67943-20-8, 75281-55-9
6-hydroxy-tetrahydro-pyrrolo[1,2-c]imidazole-1,3-dione

Conditions

Conditions	Yield
With water Eindampfen der Reaktionsloesung mit Salzsaeure;

: 79-04-9
chloroacetyl chloride

: 3398-22-9
trans-4-hydroxyproline

: 1-chloroacetyl-4-oxy-L-proline

Conditions

Conditions	Yield
With sodium hydroxide

: 3398-22-9
trans-4-hydroxyproline

: 109492-71-9, 109525-34-0
1-acetyl-4-acetoxy-L-prolin-ethyl ester

Conditions

Conditions	Yield
With hydrogenchloride Erwaermen des entstandenen Aethylesters mit Acetanhydrid und Natriumacetat;

: 7722-84-1
dihydrogen peroxide

: 7758-99-8
copper(II) sulfate

: 3398-22-9
trans-4-hydroxyproline

aqueous NaOH: aqueous NaOH

: 634-97-9
pyrrole-2-carboxyl acid

Conditions

Conditions	Yield
Behandeln des Reaktionsgemisches mit Essigsaeure und wss. HCl;

...Expand

: 3398-22-9
trans-4-hydroxyproline

: (2R,4S)-2-hydroxymethyl-4-hydroxy-N-(carbobenzyloxy)pyrrolidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: NaHCO3 / H2O 2: SOCl2 3: NaBH4; LiCl View Scheme
Multi-step reaction with 3 steps 1: NaHCO3 2: methanol 3: LiBH4 / tetrahydrofuran View Scheme

: 3398-22-9
trans-4-hydroxyproline

: 79433-95-7
(2R,4S)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaHCO3 / H2O 2: SOCl2 View Scheme
Multi-step reaction with 2 steps 1: NaHCO3 2: methanol View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / toluene; water / 16.25 h / 20 °C 1.2: pH 2 2.1: thionyl chloride / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / toluene; water / 16 h / 20 °C 1.2: pH 2 / Cooling with ice 2.1: thionyl chloride / 12 h / 0 - 20 °C View Scheme

trans-4-Hydroxy-D-proline Chemical Properties

Molecular Formula:C₅H₉NO₃Molar mass:131.12986g/mol
Structure of trans-4-Hydroxy-D-proline(3398-22-9):

Synonyms of trans-4-Hydroxy-D-proline(3398-22-9):L-Hydroxyproline;H-D-PRO(4-HYDROXY)-OH;H-D-PRO(TRANS-4-HYDROXY)-OH;H-D-HYP-OH;Proline, 4-hydroxy-;TRANS-D-HYDROXYPROLINE;4-Hydroxiproline(2R,4S)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID;
Density:1.395 g/cm³
Flash Point:168.6 °C
Boiling Point:355.2 °C at 760 mmHg
Index of Refraction:1.54
Vapour Pressure:1.8E-06 mmHg at 25°C
Melting point:260°C

trans-4-Hydroxy-D-proline Safety Profile

Hazard Codes:Xn

Risk Statements:
22: Harmful if swallowed
36: Irritating to the eyes
37: Irritating to the respiratory system
38: Irritating to the skin
43: May cause sensitization by skin contact
Safety Statements:
24: Avoid contact with skin
25: Avoid contact with eyes
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice36: Wear suitable protective clothing
37: Wear suitable gloves

trans-4-Hydroxy-D-proline Specification

Product Categories of trans-4-Hydroxy-D-proline(3398-22-9):Pyrrolidines;Carboxylic Acids;Carboxylic Acids;Chiral Compound

Product Name

trans-4-Hydroxy-D-proline

Synthetic route

trans-4-Hydroxy-D-proline Chemical Properties

trans-4-Hydroxy-D-proline Safety Profile

trans-4-Hydroxy-D-proline Specification

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