38345-66-3

Basic information

• Product Name: (2S,3R)-(+)-4-DIMETHYLAMINO-1,2-DIPHENYL-3-METHYL-2-BUTANOL
• Synonyms: (2S,3R)-(+)-4-DIMETHYLAMINO-1,2-DIPHENYL-3-METHYL-2-BUTANOL;(2S,3R)-4-DIMETHYLAMINO-1,2-DIPHENYL-3-METHYL-2-BUTANOL;(+)-(2S,3R)-4-DIMETHYLAMINO-3-METHYL-1,2-DIPHENYL-2-BUTANOL;DEXTROCARBINOL BASE;CHIRALD(R);2-S-3-R-plus-4-dimethylamino-1-2-*diphenyl-3-meth;chirald;[S-(R*,S*)]-alpha-[2-(dimethylamino)-1-methylethyl]-alpha-phenylphenethyl alcohol
• CAS NO: 38345-66-3
• Molecular Formula: C₁₉H₂₅NO
• Molecular Weight: 283.41
• EINECS: 253-893-6
• Mol File: 38345-66-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 54-56 °C(lit.)
• Boiling Point: bp0.1 mm 138-139°
• Flash Point: >230 °F
• Appearance: WHITE TO YELLOW POWDER, CRYSTALS OR SOLID
• Density: 1.043 g/cm³
• Vapor Pressure: 9.29E-08mmHg at 25°C
• Refractive Index: 1.563
• Merck: 13,2070
• BRN: 2384178
• CAS DataBase Reference: (2S,3R)-(+)-4-DIMETHYLAMINO-1,2-DIPHENYL-3-METHYL-2-BUTANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-(+)-4-DIMETHYLAMINO-1,2-DIPHENYL-3-METHYL-2-BUTANOL(38345-66-3)
• EPA Substance Registry System: (2S,3R)-(+)-4-DIMETHYLAMINO-1,2-DIPHENYL-3-METHYL-2-BUTANOL(38345-66-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 38345-66-3(Hazardous Substances Data)

Usage

Uses

Reducing reagent in organic synthesis.

Purification Methods

Purify the hydrochloride by dissolving 1.5g in 13.5 mL of 5N HCl, heat to boiling and evaporate in a vacuum. Recrystallise the hydrochloride three times from MeOH/EtOAc giving m 189-190o, []D -33.7o (c 1, H2O) {enantiomer has +34.2o}. The hydrochloride in the minimum volume of water is basified with aqueous 5N NaOH and extracted with Et2O. The extract is dried (K2CO3) and evaporated, leaving a residue which is stored in a desiccator over solid KOH as a low melting solid. It can be recovered using these procedures from asymmetric reductions with LAH, and re-used. [Pohland & Sullivan J Am Chem Soc 77 3400 1955, Sullivan et al. J Org Chem 28 2483 1963, Beilstein 13 IV 2221.]

InChI:InChI=1/C19H25NO/c1-16(15-20(2)3)19(21,18-12-8-5-9-13-18)14-17-10-6-4-7-11-17/h4-13,16,21H,14-15H2,1-3H3/t16-,19-/m1/s1

Synthetic route

(2RS,3SR)-4-dimethylamino-3-methyl-1,2-diphenyl-butan-2-ol (126-04-5, 38345-66-3, 52079-40-0, 52079-41-1, 63957-11-9, 72541-03-8) → (2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol (38345-66-3)

Conditions	Yield
With camphor-10-sulfonic acid

dimethyl amine (124-40-3) + p-toluenesulfonyl chloride (98-59-9) → (2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol (38345-66-3)

Conditions	Yield
In dimethyl sulfoxide for 48h; Ambient temperature;

formaldehyd (50-00-0) + threo-(+)-4-Amino-1,2-diphenyl-3-methyl-2-butanol-maleat → (2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol (38345-66-3)

Conditions	Yield
With formic acid

lithium aluminium tetrahydride (16853-85-3) + benzoylferrocene (1272-44-2) + (2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol (38345-66-3) → (R)-phenylhydroxymethylferrocene

Conditions	Yield
With hydrogenchloride; ammonium chloride In diethyl ether (Ar); soln. of Chirald in Et2O stirred at 0°C, added to soln. of LiAlH4 in ether, cooled to -70°C; dropwise addn. of ethereal soln. of Fe-complex at -70°C; treatment with wet ether and aq. NH4Cl;; ethereal ext. treated with 1 N HCl; crystn. (hexane);	90%

lithium aluminium tetrahydride (16853-85-3) + benzoylruthenocene + (2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol (38345-66-3) → (C5H5)Ru(C5H4CH(OH)C6H5)

Conditions	Yield
With hydrogenchloride; ammonium chloride In diethyl ether (Ar); soln. of Chirald in Et2O stirred at 0°C added to soln. of LiAlH4 in ether cooled to -70°C; dropwise addn. of ethereal soln. of Ru-complex at -50°C; treatment with wet ether and aq. NH4Cl;; ethereal ext. treated with 1 N HCl; crystn. (hexane);	90%

(2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol (38345-66-3) + binaphthol chlorophosphite (137156-22-0, 171878-71-0, 155613-52-8) → (1'S,2'R)-2-(1'-benzyl-3'-dimethylamino-2'-methyl-1'-phenyl-propoxy)dinaphtho[2,1-d:1',2'-f](1,3,2) dioxaphosphepine (479253-09-3)

Conditions	Yield
With triethylamine In toluene	89%

(2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol (38345-66-3) + [(R)-1,1'-binaphthyl-2,2'-diyl]chlorophosphite → (Rax)-(1'S,2'R)-2-(1'-benzyl-3'-dimethylamino-2'-methyl-1'-phenyl-propoxy)dinaphtho[2,1-d:1',2'-f](1,3,2) dioxaphosphepine

Conditions	Yield
With triethylamine In toluene	87%

(2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol (38345-66-3) + 1-dodecylbromide (143-15-7) → (+)-(2R,3S)-N-(3-hydroxy-2-methyl-3,4-diphenylbutyl)-N,N-dimethyldodecan-1-ammonium bromide (1356938-68-5)

Conditions	Yield
In acetonitrile for 240h; Reflux;	65%

(2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol (38345-66-3) + benzyl chloride (100-44-7) → (2R,3S)-(+)N-benzyl-N,N-dimethyl-N-(3,4-diphenyl-3-hydroxy-2-methylbutyl) ammonium chloride

Conditions	Yield
In ethanol for 18h; Heating;	28%

methyl 2-oxo-2-phenylacetate (15206-55-0) + (2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol (38345-66-3) + lithium tetrabutylaluminate (14263-32-2) → α-butyl-α-hydroxy phenyl methyl ester (75844-45-0, 97690-16-9)

Conditions	Yield
With hydrogenchloride In hexane at 0℃; for 2h; asymmetric alkylation; various solvent;
With hydrogenchloride Multistep reaction;

diazoacetic acid ethyl ester (623-73-4) + dimethylmonochlorosilane (1066-35-9) + (2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol (38345-66-3) → [((1S,2R)-1-Benzyl-3-dimethylamino-2-methyl-1-phenyl-propoxy)-dimethyl-silanyl]-acetic acid ethyl ester

Conditions	Yield
With dirhodium tetraacetate; triethylamine 1.) CH2Cl2, room temperature, 2.) CH2Cl2, room temperature, 2 h; Yield given. Multistep reaction;

(2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol (38345-66-3) → 2-[((1S,2R)-1-Benzyl-3-dimethylamino-2-methyl-1-phenyl-propoxy)-dimethyl-silanyl]-propionic acid ethyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) Rh2(OAc)4, 2.) NEt3 / 1.) CH2Cl2, room temperature, 2.) CH2Cl2, room temperature, 2 h 2: hexamethyldisilazane, n-BuLi / hexane; tetrahydrofuran / 1.) -50 deg C, 2 h, 2.) -80 deg C, 2 h View Scheme

lithium aluminium tetrahydride (16853-85-3) + 1,1’-dibenzoylferrocene (12180-80-2, 32983-90-7) + (2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol (38345-66-3) → (+/-), meso-1,1'-bis(α-hydroxybenzyl)ferrocene

Conditions	Yield
With ammonium chloride In diethyl ether (Ar); soln. of Chirald in Et2O stirred at 0°C added to soln. of LiAlH4 in ether cooled to -70°C; dropwise addn. of ethereal soln. of Fe-complex at -20°C; treatment with wet ether and aq. NH4Cl;; rapid chromy. (Al2O3, ether); crystn. (heptane);	>99

lithium aluminium tetrahydride (16853-85-3) + 1,1'-dibenzoylruthenocene + (2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol (38345-66-3) → (C5H4CH(OH)C6H5)Ru(C5H4CH(OH)C6H5)

Conditions	Yield
With hydrogenchloride; ammonium chloride In diethyl ether (Ar); soln. of Chirald in Et2O stirred at 0°C added to soln. of LiAlH4 in ether cooled to -70°C; dropwise addn. of ethereal soln. of Ru-complex at -20°C; treatment with wet ether and aq. NH4Cl; ethereal ext. treated with HCl;; crystn. (heptane or hexane);	>99

(2RS)-3,3,3-trifluoro-2-methylpropanoic acid (381-97-5) + (2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol (38345-66-3) → C4H5F3O2*C19H25NO + C4H5F3O2*C19H25NO

Conditions	Yield
In isopropyl alcohol at 20 - 70℃;	A n/a B n/a

Upstream product

• 124-40-3 dimethyl amine 
• 98-59-9 p-toluenesulfonyl chloride 
• 91-03-2 3-dimethylamino-2-methyl-1-phenyl-propan-1-one 
• 6921-34-2 benzylmagnesium chloride 
• 50-00-0 formaldehyd 
• 126-04-5 (2RS,3SR)-4-dimethylamino-3-methyl-1,2-diphenyl-butan-2-ol 

Downstream Products

• 72541-03-8 (2R,3S)-(-)-4-dimethylamino-1,2-diphenyl-3-methyl-2-butanol 
• 75844-45-0 α-butyl-α-hydroxy phenyl methyl ester 
• 24274-73-5 (E)-1,2-diphenyl-2-butene 
• 1356938-68-5 (+)-(2R,3S)-N-(3-hydroxy-2-methyl-3,4-diphenylbutyl)-N,N-dimethyldodecan-1-ammonium bromide 
• 479253-09-3 (1'S,2'R)-2-(1'-benzyl-3'-dimethylamino-2'-methyl-1'-phenyl-propoxy)dinaphtho[2,1-d:1',2'-f](1,3,2) dioxaphosphepine 
• 52016-49-6 dimethyl-(2-methyl-3,4-diphenyl-but-2-enyl)-amine 

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