5267-64-1

Basic information

• Product Name: D(+)-Phenylalaninol
• Synonyms: D-(+)-Phenylalinol;S/R-Phenylalaninol;(2R)-2-amino-3-phenylpropan-1-ol;D-Penylalaninol;D-PHEYLALANINOL;D-PHENYLANINOL;(D)-(+)-2-PHENYLALANINOL / D-(+)-2-AMINO-3-PHENYL-1-PROPANOL;D-Phenylalaninol(R+Phenylalaninol)
• CAS NO: 5267-64-1
• Molecular Formula: C₉H₁₃NO
• Molecular Weight: 151.21
• EINECS: 226-086-1
• Product Categories: Pharmaceutical Intermediates;chiral;Phenylalanine [Phe, F];Amino Alcohols (Chiral);Chiral Building Blocks;Synthetic Organic Chemistry;Amino alcohols
• Mol File: 5267-64-1.mol
• Article Data: 97

Chemical Properties

• Melting Point: 93-95 °C(lit.)
• Boiling Point: 122 °C / 4mmHg
• Flash Point: 139.8 °C
• Appearance: White to yellow/Crystalline Powder and Chunks
• Density: 1.0406 (rough estimate)
• Vapor Pressure: 0.000779mmHg at 25°C
• Refractive Index: 23.5 ° (C=1.2, 1mol/L HCl)
• Storage Temp.: 0-6°C
• Solubility: Soluble in Dichloromethane, Ethyl Acetate, Methanol.
• PKA: 12.85±0.10(Predicted)
• Sensitive: Air Sensitive
• BRN: 4665408
• CAS DataBase Reference: D(+)-Phenylalaninol(CAS DataBase Reference)
• NIST Chemistry Reference: D(+)-Phenylalaninol(5267-64-1)
• EPA Substance Registry System: D(+)-Phenylalaninol(5267-64-1)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34
• Safety Statements: 26-36/37/39-45-27
• RIDADR: UN 3259 8/PG 3
• WGK Germany: 3
• F: 10-23
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 5267-64-1(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

D-Phenylalaninol is used as a chiral auxiliary for asymmetric Michael reactions. It is an enantiomer of L-Phenylalaninol, an inhibitor of intestinal Phenylalanine absorption. It acts as an inhibiting agent to the enzymes which are responsible for the breakdown of endorphins.

InChI:InChI=1/C9H13NO/c1-9(10,7-11)8-5-3-2-4-6-8/h2-6,11H,7,10H2,1H3/t9-/m1/s1

Synthetic route

D-(R)-phenylalanine (673-06-3) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
With lithium borohydride; chloro-trimethyl-silane In tetrahydrofuran at 20℃; for 0.25h; Reduction;	99%
With sodium tetrahydroborate; iodine In tetrahydrofuran at 0℃; Reflux;	99%
With sodium tetrahydroborate; sulfuric acid In tetrahydrofuran at 20℃;	98%

(R)-N-(1-hydroxy-3-phenylpropan-2-yl)acetamide → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
With sulfuric acid In water at 120℃;	98%
With sulfuric acid at 100℃; for 48h; Darkness;	143.7 mg

(R)-2-amino-3-phenylpropionitrile hydrochloride → (R)-2-amino-3-phenylpropanol (5267-64-1) + (R)-3-phenylpropane-1,2-diamine (85612-59-5)

Conditions	Yield
With hydrogenchloride; methanol; water; hydrogen; 5% palladium over charcoal at 35℃; under 6750.68 - 22502.3 Torr; for 43h;	A 91% B 6%

(R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2, 90719-32-7, 120574-96-1, 102029-44-7) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
With ammonium bromide; 3-azapentane-1,5-diamine at 90℃; for 5h; Microwave irradiation;	84%

9H-fluoren-9-ylmethyl (R)-<1-(hydroxymethyl)-2-phenylethyl>carbamate (130406-30-3) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
With piperidine In dichloromethane for 1h; Ambient temperature;	82%

D-phenylalanine methyl ester (21685-51-8) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
With methanol; sodium tetrahydroborate at 0 - 10℃; for 1h; Temperature; Solvent;	81%

(1R,1'R)-N,1'-dibenzyl-1-phenyl-2,2'-dihydroxydiethylamine → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
With ammonium formate; palladium on activated charcoal In methanol for 2h; Heating;	80%

(+)-(R)-2-(1-benzyl-2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione (152903-44-1) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
With hydrazine hydrate In acetonitrile for 4h; Heating;	73%

rac-phenylalaninol (1795-98-8, 3182-95-4, 5267-64-1, 16088-07-6) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
Stage #1: rac-phenylalaninol With O,O'-dibenzoyl-L-tartaric acid In acetone at 25℃; for 6h; Stage #2: With potassium hydroxide In dichloromethane	52%

(L)-phenylalanine ethyl ester hydrochloride (3182-93-2) → L-Phenylalaninol (3182-95-4) + (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
With methanol; Na/SiO2 In tetrahydrofuran at 0 - 25℃; Bouveault-Blanc reduction; Inert atmosphere; optical yield given as %ee;	A 27% B n/a

D-phenylalanine ethyl ester (1795-96-6, 3081-24-1, 20529-91-3) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether

methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran

rac-phenylalaninol (1795-98-8, 3182-95-4, 5267-64-1, 16088-07-6) + (2R)-mandelamide (4358-86-5, 4410-31-5, 24008-63-7, 24008-62-6) → L-Phenylalaninol (3182-95-4) + (R)-2-amino-3-phenylpropanol (5267-64-1) + (R)-Mandelic Acid (611-71-2) + (R)-N-<(S)-1-benzyl-2-hydroxyethyl>mandelamide (113336-57-5)

Conditions	Yield
With Alcaligenes PA In water at 25℃; pH=10;

ethyl 2-(hydroxyimino)-3-phenylpropanoate (6943-96-0, 70564-52-2, 70564-53-3) → (R)-2-amino-3-phenylpropanol (5267-64-1) + O=CH(CH2)2NHCOO-Wang-polystyrene

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 80 percent / NaBH4; I2 / tetrahydrofuran / 4 h / Heating 2.1: dibenzoyl-L-tartaric acid / acetone / 6 h / 25 °C 2.2: 52 percent / aq. KOH / CH2Cl2 View Scheme

Boc-D-Phe-OH (18942-49-9) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: BH3*THF 2: H3O(1+) View Scheme

Hydroxymethyl-((R)-1-hydroxymethyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester (210561-40-3) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / NaOH / methanol; H2O / Ambient temperature 2: H3O(1+) View Scheme

(1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 93 percent / xylene / 2 h / Heating 2: 1.) SOCl2, 2.) LiBr / 1.) CHCl3, 8 h, 2.) Me2CO, 6 h 3: 80 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 4: 73 percent / NH2NH2*H2O / acetonitrile / 4 h / Heating View Scheme
Multi-step reaction with 5 steps 1: 93 percent / xylene / 2 h / Heating 2: 60 percent / SOCl2, Et3N / CH2Cl2 / 1 h / 0 °C 3: 60 percent / LiBr, PTSA / acetonitrile / 2 h / Ambient temperature 4: 80 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 5: 73 percent / NH2NH2*H2O / acetonitrile / 4 h / Heating View Scheme

(1S,2S)-1-phenyl-2-phthalimido-propane-1,3-diol (123537-84-8) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) SOCl2, 2.) LiBr / 1.) CHCl3, 8 h, 2.) Me2CO, 6 h 2: 80 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 3: 73 percent / NH2NH2*H2O / acetonitrile / 4 h / Heating View Scheme
Multi-step reaction with 4 steps 1: 60 percent / SOCl2, Et3N / CH2Cl2 / 1 h / 0 °C 2: 60 percent / LiBr, PTSA / acetonitrile / 2 h / Ambient temperature 3: 80 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 4: 73 percent / NH2NH2*H2O / acetonitrile / 4 h / Heating View Scheme

2-((S)-2-Bromo-1-hydroxymethyl-2-phenyl-ethyl)-isoindole-1,3-dione → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 2: 73 percent / NH2NH2*H2O / acetonitrile / 4 h / Heating View Scheme

2-((4S,5S)-2-Oxo-4-phenyl-2λ4-[1,3,2]dioxathian-5-yl)-isoindole-1,3-dione (176538-77-5) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 60 percent / LiBr, PTSA / acetonitrile / 2 h / Ambient temperature 2: 80 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 3: 73 percent / NH2NH2*H2O / acetonitrile / 4 h / Heating View Scheme

(4R,4R)-N,2-dibenzyl-4-phenyl-1,3-oxazolidine → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2.) KF, NaHCO3, 30percent H2O2 / 1.) THF, RT, 24 h, 2.) THF, methanol, RT, 48 h 2: 80 percent / HCO2NH4 / 10percent Pd-C / methanol / 2 h / Heating View Scheme

(-)-(R)-(N-9-fluorenylmethoxycarbonyl)phenylalaninal (146803-47-6) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / sodium borohydride / tetrahydrofuran / 2 h / 0 °C 2: 82 percent / piperidine / CH2Cl2 / 1 h / Ambient temperature View Scheme

(R)-dibenzyl 1-(1-hydroxy-3-phenylpropan-2-yl)hydrazine-1,2-dicarboxylate (438470-79-2) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
With hydrogen; nickel In methanol; acetic acid at 25℃; under 3102.97 Torr; for 20h;

(R)-2-nitro-3-phenylpropan-1-ol (1255037-12-7) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
With sulfuric acid; zinc In water

rac-phenylalaninol (1795-98-8, 3182-95-4, 5267-64-1, 16088-07-6) → L-Phenylalaninol (3182-95-4) + (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
With chiral stationary phase including isopropyl-functionalized CF6 In methanol; acetic acid; triethylamine; acetonitrile at 20℃; Purification / work up;
With C45H31O4P In aq. phosphate buffer; chloroform at 6℃; for 16h; Reagent/catalyst; Sealed tube; Resolution of racemate;
With (S)-(+)-3,3'-diphenyl-2,2'-bi-1-naphthol hydrogen phosphate In aq. phosphate buffer; chloroform; water at 6℃; for 16h; pH=5; Reagent/catalyst; enantioselective reaction;	A n/a B n/a

α-Acetamido-cinnamaldehyd (3548-71-8) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: (R,R)-(-)-2,3-bis(tert-butylmethylphosphino)benzene; di[(η-1,2,5,6)-1,5-cyclooctadiene] rhodium hexafluoroantimonate; hydrogen / dichloromethane / 12 h / 20 °C / Autoclave 2: sulfuric acid / 48 h / 100 °C / Darkness View Scheme
Multi-step reaction with 2 steps 1: di[(η-1,2,5,6)-1,5-cyclooctadiene] rhodium hexafluoroantimonate; hydrogen; (R)-1-[(Sp)-2-(diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine / dichloromethane / 4 h / 20 °C / 22801.5 Torr / Autoclave 2: sulfuric acid / 48 h / 100 °C / Darkness View Scheme
Multi-step reaction with 3 steps 1: (R,R)-(-)-2,3-bis(tert-butylmethylphosphino)benzene; di[(η-1,2,5,6)-1,5-cyclooctadiene] rhodium hexafluoroantimonate; hydrogen / ethyl acetate / 4 h / 20 °C / 22801.5 Torr / Autoclave 2: sodium tetrahydroborate 3: sulfuric acid / 48 h / 100 °C / Darkness View Scheme
Multi-step reaction with 3 steps 1: (R,R)-(-)-2,3-bis(tert-butylmethylphosphino)benzene; di[(η-1,2,5,6)-1,5-cyclooctadiene] rhodium hexafluoroantimonate; hydrogen / dichloromethane / 4 h / 20 °C / Autoclave 2: sodium tetrahydroborate 3: sulfuric acid / 48 h / 100 °C / Darkness View Scheme
Multi-step reaction with 3 steps 1: di[(η-1,2,5,6)-1,5-cyclooctadiene] rhodium hexafluoroantimonate; hydrogen; (R)-1-[(Sp)-2-(diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine / dichloromethane / 4 h / 20 °C / 22801.5 Torr / Autoclave 2: sodium tetrahydroborate 3: sulfuric acid / 48 h / 100 °C / Darkness View Scheme

(R)-N-(1-oxo-3-phenylpropan-2-yl)acetamide → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate 2: sulfuric acid / 48 h / 100 °C / Darkness View Scheme

di-tert-butyl dicarbonate (24424-99-5) + (R)-2-amino-3-phenylpropanol (5267-64-1) → N-tert-butoxycarbonyl-D-Phenylalaninol (106454-69-7)

Conditions	Yield
In dichloromethane at 0 - 20℃;	100%
In ethanol at 30℃; for 0.0166667h;	99%
In chloroform at 0 - 20℃; Substitution;	95%

(R)-2-amino-3-phenylpropanol (5267-64-1) + chloroacetyl chloride (79-04-9) → 2-chloro-N-(1-hydroxymethyl-2-phenyl-ethyl)-acetamide (466695-52-3)

Conditions	Yield
With triethylamine In tetrahydrofuran at 25℃;	100%

tert-butyldicarbonate (34619-03-9) + (R)-2-amino-3-phenylpropanol (5267-64-1) → N-tert-butoxycarbonyl-D-Phenylalaninol (106454-69-7)

Conditions	Yield
With sodium hydroxide In dichloromethane; water at 20℃; for 24h;	100%

(R)-2-amino-3-phenylpropanol (5267-64-1) → 1-chloro-2(R)-amino-phenylpropane hydrochloride (100431-27-4)

Conditions	Yield
With thionyl chloride In N,N-dimethyl-formamide at 120℃; for 2h;	99%

(R)-2-amino-3-phenylpropanol (5267-64-1) + methyl chloroformate (79-22-1) → R-(+)-N,O-bis(methoxycarbonyl)-2-amino-3-phenylpropanol (252659-50-0)

Conditions	Yield
With pyridine In chloroform at 20℃; for 14h; Condensation;	99%

(R)-(-)-1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-2,2'-binaphthyl-8,8'-dicarbaldehyde + (R)-2-amino-3-phenylpropanol (5267-64-1) → C48H52N2O8

Conditions	Yield
In methanol at 20℃; for 3h; Inert atmosphere; optical yield given as %de;	99%

(R)-2-amino-3-phenylpropanol (5267-64-1) + 4-bromobenzenesulfonyl chloride (98-58-8) → (R)-4-bromo-N-(1-hydroxy-3-phenylpropan-2-yl)benzenesulfonamide

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 1h;	99%

(R)-2-amino-3-phenylpropanol (5267-64-1) + 2,2-Dimethylmalonyl chloride (5659-93-8) → (R,R)-N,N'-bis(1-benzyl-2-hydroxyethyl)-2,2-dimethylpropane-1,3-diamide

Conditions	Yield
With triethylamine In dichloromethane 0 deg C, 30 min; 23 deg C, 2 h;	97%

carbon dioxide (124-38-9) + (R)-2-amino-3-phenylpropanol (5267-64-1) → (R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2, 90719-32-7, 120574-96-1, 102029-44-7)

Conditions	Yield
With triethylamine; chlorophosphoric acid diphenyl ester In acetonitrile at -40 - 25℃;	97%
Stage #1: carbon dioxide; (R)-2-amino-3-phenylpropanol With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 0.75h; Stage #2: With tributylphosphine; di-tert-butyl-diazodicarboxylate In acetonitrile at 0℃; for 0.333333h; Mitsunobu reaction;	78%
With tetramethylphenylguanidine; diphenyl phosphoryl azide In acetonitrile at -40 - 20℃;	75%

phthalic anhydride (85-44-9) + (R)-2-amino-3-phenylpropanol (5267-64-1) → (+)-(R)-2-(1-benzyl-2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione (152903-44-1)

Conditions	Yield
at 140℃;	96%
With triethylamine In toluene for 3h; Condensation; Heating;	93%
at 200℃; for 3h;	91%
at 140 - 150℃; for 6h;	82%

(R)-2-amino-3-phenylpropanol (5267-64-1) + 6-methoxy-4-((1R)-methoxy((1S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)quinoline-2-carboxyli c acid → N-((R)-1-hydroxy-3-phenylpropan-2-yl)-6-methoxy-4-((1R)-methoxy((1S,4S,5R)-5-vinylquin uclidin-2-yl)methyl)quinoline-2-carboxamide

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Cooling with ice;	96%

(R)-2-amino-3-phenylpropanol (5267-64-1) + 4,6-dichloro-1-phenyl-1H-pyrazolo<3,4-d>pyrimidine (99971-84-3) → (R)-β-<(1-phenyl-6-chloro-1H-pyrazolo<3,4-d>pyrimidin-4-yl)amino>benzenepropanol (132537-83-8)

Conditions	Yield
In ethanol for 48h; Ambient temperature;	95%
In ethanol	95%

(R)-2-amino-3-phenylpropanol (5267-64-1) + benzoyl chloride (98-88-4) → N-benzoyl-D-phenylalaninol (5267-65-2)

Conditions	Yield
With potassium carbonate In methanol at 20℃;	95%
With potassium carbonate In methanol at 20℃;	95%
With potassium carbonate In methanol at 20℃;	95%
With potassium carbonate In methanol at 20℃; Acylation;
With potassium carbonate In methanol at 20℃;

4-Chloro-2-phenyl-7-propyl-2H-pyrazolo[3,4-d]pyrimidin-6(7H)-one (791071-50-6) + (R)-2-amino-3-phenylpropanol (5267-64-1) → (R)-4-(1-hydroxy-3-phenylprop-2-ylamino)-2-phenyl-7-propyl-2H-pyrazolo[3,4-d]pyrimidin-6(7H)-one (791071-43-7)

Conditions	Yield
In isopropyl alcohol Heating / reflux;	95%

(2-oxocyclopent)acetic acid (104115-44-8) + (R)-2-amino-3-phenylpropanol (5267-64-1) → (3R,5aR,8aS)-3-benzyl-hexahydro-1-oxa-3a-aza-cyclopenta[c]pentalen-4-one (1240492-77-6)

Conditions	Yield
at 110℃; under 11251.1 Torr; Meyer synthesis; Microwave irradiation; optical yield given as %de;	95%
In water at 100℃; for 16h;	80%

(R)-2-amino-3-phenylpropanol (5267-64-1) + (1S,4S,5S,7R)-5-chloro-7-((6-chloro-9H-purin-9-yl)methyl)bicyclo[2.2.1]heptan-2-ol → (1S,4S,5S,7R)-5-chloro-7-((6-(((R)-1-hydroxy-3-phenylpropan-2-yl)amino)-9H-purin-9-yl)methyl)bicyclo[2.2.1]heptan-2-ol

Conditions	Yield
With triethylamine In ethanol at 60℃; for 72h;	94.1%

(R)-2-amino-3-phenylpropanol (5267-64-1) + Boc-Phe-ONSu (3674-06-4) → tert-butyl ((2S)-1-(((2R)-1-hydroxy-3-phenylpropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (138772-68-6)

Conditions	Yield
With triethylamine In tetrahydrofuran Ambient temperature;	94%

9-Chloroacridine (1207-69-8) + (R)-2-amino-3-phenylpropanol (5267-64-1) → (R)-2-(Acridin-9-ylamino)-3-phenyl-propan-1-ol

Conditions	Yield
In various solvent(s) at 80 - 85℃; for 2h;	94%

(R)-2-amino-3-phenylpropanol (5267-64-1) + (S)-(+)-1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-2,2'-binaphthyl-8,8'-dicarbaldehyde → C48H52N2O8

Conditions	Yield
In methanol at 20℃; for 3h; Inert atmosphere; optical yield given as %de;	94%

(R)-2-amino-3-phenylpropanol (5267-64-1) + tert-butyl N-{2-[4-(isothiocyanatomethyl)benzamido]phenyl}carbamate (1448350-40-0) → tert-butyl N-(2-{4-[({[(2R)-1-hydroxy-3-phenylpropan-2-yl]carbamothioyl}amino)methyl]benzamido}phenyl)carbamate (1448350-45-5)

Conditions	Yield
In acetonitrile at 20℃; for 16h;	94%
In tetrahydrofuran at 20℃; for 16h;

(R)-2-amino-3-phenylpropanol (5267-64-1) + 1,2-bis(dicyclohexylamino)-3-chlorocyclopropenium chloride → (R)-2-(2,3-bis(dicyclohexylamino)cyclopropenimine)-3-phenylpropan-1-ol hydrochloride (1620078-17-2)

Conditions	Yield
Stage #1: (R)-2-amino-3-phenylpropanol; 1-chloro-2,3-bis(dicyclohexylamino)cyclopropenium chloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 23℃; for 12h; Stage #2: With hydrogenchloride In dichloromethane	93%

thiophene-2-carbaldehyde (98-03-3) + (R)-2-amino-3-phenylpropanol (5267-64-1) → (R)-3-phenyl-2-[(thien-2-ylmethyl)amino]propan-1-ol

Conditions	Yield
Stage #1: thiophene-2-carbaldehyde; (R)-2-amino-3-phenylpropanol In methanol at 20℃; Stage #2: With sodium tetrahydroborate In ethanol at 0℃; Further stages.;	92%

D-(R)-phenylalanine (673-06-3) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
With lithium borohydride; chloro-trimethyl-silane In tetrahydrofuran at 20℃; for 0.25h; Reduction;	99%
With sodium tetrahydroborate; iodine In tetrahydrofuran at 0℃; Reflux;	99%
With sodium tetrahydroborate; sulfuric acid In tetrahydrofuran at 20℃;	98%

(R)-N-(1-hydroxy-3-phenylpropan-2-yl)acetamide → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
With sulfuric acid In water at 120℃;	98%
With sulfuric acid at 100℃; for 48h; Darkness;	143.7 mg

(R)-2-amino-3-phenylpropionitrile hydrochloride → (R)-2-amino-3-phenylpropanol (5267-64-1) + (R)-3-phenylpropane-1,2-diamine (85612-59-5)

Conditions	Yield
With hydrogenchloride; methanol; water; hydrogen; 5% palladium over charcoal at 35℃; under 6750.68 - 22502.3 Torr; for 43h;	A 91% B 6%

(R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2, 90719-32-7, 120574-96-1, 102029-44-7) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
With ammonium bromide; 3-azapentane-1,5-diamine at 90℃; for 5h; Microwave irradiation;	84%

9H-fluoren-9-ylmethyl (R)-<1-(hydroxymethyl)-2-phenylethyl>carbamate (130406-30-3) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
With piperidine In dichloromethane for 1h; Ambient temperature;	82%

D-phenylalanine methyl ester (21685-51-8) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
With methanol; sodium tetrahydroborate at 0 - 10℃; for 1h; Temperature; Solvent;	81%

(1R,1'R)-N,1'-dibenzyl-1-phenyl-2,2'-dihydroxydiethylamine → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
With ammonium formate; palladium on activated charcoal In methanol for 2h; Heating;	80%

(+)-(R)-2-(1-benzyl-2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione (152903-44-1) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
With hydrazine hydrate In acetonitrile for 4h; Heating;	73%

rac-phenylalaninol (1795-98-8, 3182-95-4, 5267-64-1, 16088-07-6) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
Stage #1: rac-phenylalaninol With O,O'-dibenzoyl-L-tartaric acid In acetone at 25℃; for 6h; Stage #2: With potassium hydroxide In dichloromethane	52%

(L)-phenylalanine ethyl ester hydrochloride (3182-93-2) → L-Phenylalaninol (3182-95-4) + (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
With methanol; Na/SiO2 In tetrahydrofuran at 0 - 25℃; Bouveault-Blanc reduction; Inert atmosphere; optical yield given as %ee;	A 27% B n/a

D-phenylalanine ethyl ester (1795-96-6, 3081-24-1, 20529-91-3) → (R)-2-amino-3-phenylpropanol (5267-64-1)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether

Upstream product

• 4134-09-2 ethyl N-acetyl-DL-phenylalaninate 
• 3532-57-8 acetic acid-(β-nitro-cinnamyl ester) 
• 150-30-1 Phenylalanine 
• 673-06-3 (+)-phenylalanine 
• 13906-90-6 2-benzylaziridine 
• 3182-93-2 ethyl 2-amino-3-phenylpropanoate hydrochloride 
• 5619-07-8 methyl 2-amino-3-phenylpropanoate hydrochloride 
• 303727-83-5 (-)-(R)-4-benzyl-3-((2R,3S,4S)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentanoyl)oxazolidin-2-one 
• 104-54-1 3-Phenylpropenol 
• 152903-44-1 (+)-(R)-2-(1-benzyl-2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione 
• 438470-79-2 (R)-dibenzyl 1-(1-hydroxy-3-phenylpropan-2-yl)hydrazine-1,2-dicarboxylate 
• 1255037-12-7 (R)-2-nitro-3-phenylpropan-1-ol 
• 1795-98-8 rac-phenylalaninol 
• 21685-51-8 D-phenylalanine methyl ester 

Downstream Products

• 765887-92-1 1-bromomethyl-2-phenyl-ethylamine 
• 20826-32-8 2-(2,4-dinitro-anilino)-3-phenyl-propan-1-ol 
• 91427-72-4 dichloro-acetic acid-(1-hydroxymethyl-2-phenyl-ethylamide) 
• 140145-71-7 1-(1-Benzyl-2-hydroxyethyl)-pyrrolidin 
• 138772-66-4 N-t-BOC-D-Phe-D-phenylalaninol 
• 72782-19-5 (R)-(+)-N-dansylphenylalaninol 
• 130406-30-3 9H-fluoren-9-ylmethyl (R)-<1-(hydroxymethyl)-2-phenylethyl>carbamate 
• 144862-85-1 (R)-2-(6-Chloro-2-methoxy-acridin-9-ylamino)-3-phenyl-propan-1-ol 
• 19881-92-6 rac-N-(1-hydroxy-3-phenylpropan-2-yl)acetamide 
• 145059-73-0 2-amino-3-phenyl-propanol-1-acetate 
• 73058-30-7 (2S)-2-benzylazacyclopropane 
• 91373-80-7 N-isopropyl-D-phenylalaninol 
• 138772-68-6 tert-butyl ((2S)-1-(((2R)-1-hydroxy-3-phenylpropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate 
• 101629-89-4 (+)-N-<(R)-α-(hydroxymethyl)phenethyl>-2-methylpropenamide 

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