79069-13-9

Basic information

• Product Name: N-Boc-L-alaninol
• Synonyms: N-BOC-S-ALANINOL;N-ALPHA-T-BOC-L-ALANINOL;N-ALPHA-TERT-BUTYLOXYCARBONYL-L-ALANINOL;N-T-BUTOXYCARBONYL-L-ALANINOL;N-T-BOC-L-ALANINOL;N-TERT-BUTOXYCARBONYL-L-ALANINOL;Boc-Ala-ol~(S)-2-(Boc-amino)-1-propanol~N-(tert-Butoxycarbonyl)-L-alaninol;Butoxycarbonylalaninol
• CAS NO: 79069-13-9
• Molecular Formula: C₈H₁₇NO₃
• Molecular Weight: 175.23
• EINECS: 1533716-785-6
• Product Categories: N-BOC;straight chain compounds;Amino Acids;Amino Alcohols;Boc-Amino acid series;Heterocyclic Acids,Indolines ,Indoles ,Indazoles
• Mol File: 79069-13-9.mol
• Article Data: 173

Chemical Properties

• Melting Point: 59-62 °C(lit.)
• Boiling Point: 276.4 °C at 760 mmHg
• Flash Point: 121 °C
• Appearance: White/Crystalline Powder or Lumps
• Density: 1.025 g/cm³
• Vapor Pressure: 0.000597mmHg at 25°C
• Refractive Index: -8.6 ° (C=1.2, MeOH)
• Storage Temp.: 2-8°C
• Solubility: almost transparency in Methanol
• PKA: 12.11±0.46(Predicted)
• BRN: 3648840
• CAS DataBase Reference: N-Boc-L-alaninol(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-L-alaninol(79069-13-9)
• EPA Substance Registry System: N-Boc-L-alaninol(79069-13-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 9-21
• Hazardous Substances Data: 79069-13-9(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

InChI:InChI=1/C8H17NO3/c1-6(5-10)9-7(11)12-8(2,3)4/h6,10H,5H2,1-4H3,(H,9,11)/t6-/m0/s1

Synthetic route

(S)-Alaninol (2749-11-3) + di-tert-butyl dicarbonate (24424-99-5) → (S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane at 20℃; for 3h;	100%
With triethylamine In methanol at 20℃; for 12h;	100%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 12h;	100%

(S)-N-(tert-butoxycarbonyl)alanine methyl ester (28875-17-4) → (S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9)

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran; methanol at 65℃; for 1h;	100%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;	97%
With RuH(η1-BH4)(dppp)((R,R)-dpen); hydrogen In tetrahydrofuran at 80℃; under 37503.8 Torr; for 16h; Autoclave;	96%

(S)-2-aminobutan-1-ol (5856-62-2) + di-tert-butyl dicarbonate (24424-99-5) → (S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; for 6h; Inert atmosphere;	97%

L-N-Boc-Ala (15761-38-3) → (S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9)

Conditions	Yield
With borane-THF In tetrahydrofuran at 0℃; other substrates, also with LiAlH4 and DIBAL;	95%
With borane-THF In tetrahydrofuran at 0℃;	95%
Stage #1: L-N-Boc-Ala With 4-methyl-morpholine; 1,3,5-trichloro-2,4,6-triazine In 1,2-dimethoxyethane at 20℃; for 3h; Esterification; Stage #2: With sodium tetrahydroborate In water at 0℃; Reduction;	90%

N-(tert-butoxycarbonyl)-L-alanine pentachlorophenyl ester (17693-17-3) → (S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9)

Conditions	Yield
With sodium tetrahydroborate; iodine In tetrahydrofuran at 20℃; Reduction;	89%

(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)propan-2-ylcarbamate (909297-88-7) → (S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9)

Conditions	Yield
With sodium hydrogen sulfate; silica gel In dichloromethane at 20℃; for 0.5h;	89%

D-Alanine (338-69-2) + di-tert-butyl dicarbonate (24424-99-5) → (S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9)

Conditions	Yield
Stage #1: D-Alanine With lithium aluminium tetrahydride In tetrahydrofuran for 12h; Reflux; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; dichloromethane; water at 60℃; for 6h;	63%

(-)-tert-butyl [(1S)-1-methylprop-2-en-1-yl]carbamate (115378-33-1) → (S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9)

Conditions	Yield
Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1.1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / water; acetone / 16 h / 20 °C 1.2: 20 °C 2.1: sodium tetrahydroborate / diethyl ether; methanol / 20 °C View Scheme

N2-Boc-L-alanine ethoxycarbonic anhydride → (S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9)

Conditions	Yield
With sodium tetrahydroborate In methanol Yield given;

Boc-Ala-O-N-hydroxysuccinimide (3392-05-0) → (S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9)

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran at 20℃; for 2.5h;
With sodium tetrahydroborate In water at 0℃;	0.28 g

C12H21NO6 (118517-03-6) → (S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9)

Conditions	Yield
With sodium tetrahydroborate In water at 0℃;

L-N-Boc-Ala (15761-38-3) + resin-bond orthogonally protected Fmoc-Lys-(Boc) → (S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: NEt3 / tetrahydrofuran / -10 °C 2: NaBH4 / H2O / 0 °C View Scheme
Multi-step reaction with 2 steps 1: 77 percent / EDC / CH2Cl2 / 16 h / -8 - 4 °C 2: NaBH4 / tetrahydrofuran / 2.5 h / 20 °C View Scheme

di-tert-butyl dicarbonate (24424-99-5) → (S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. NaOH / dioxane / 20 °C 2: NEt3 / tetrahydrofuran / -10 °C 3: NaBH4 / H2O / 0 °C View Scheme
Multi-step reaction with 2 steps 1: 97 percent / NaHCO3; NaCl / CHCl3; H2O / 3 h / Heating 2: 91 percent / NaBH4; LiCl / tetrahydrofuran; ethanol / 16 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: triethylamine / tetrahydrofuran / 20 - 50 °C 2.1: lithium aluminum hydride / tetrahydrofuran / 0.33 h 2.2: aq. potassium hydroxide / tetrahydrofuran / 1 h / 20 °C View Scheme

Boc-Ala-H (79069-50-4) → (S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) zinc, AlMe3 / 1.) THF, hexane, 25 deg C, 15 min, 2.) -30 to -20 deg C, 5 h View Scheme
With lithium borohydride
With sodium tetrahydroborate
With sodium tetrahydroborate In methanol; diethyl ether at 20℃;	51.8 mg

(S)-Alaninol (2749-11-3) + tert-butyldicarbonate (34619-03-9) + 1,1-dimethylethylenediamine (811-93-8) → (S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9)

Conditions	Yield
In water; tert-butyl alcohol

Boc-Ala-O-COO-isoBu (109208-68-6) → (S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9)

Conditions	Yield
With sodium tetrahydroborate In water Inert atmosphere;
With sodium tetrahydroborate In tetrahydrofuran; water at 0 - 20℃;

iminodicarboxylic acid di-tert-butyl ester (51779-32-9) → (S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine / tetrahydrofuran / 0.08 h / Inert atmosphere; Schlenk technique 1.2: 1 h / 50 °C / Inert atmosphere; Schlenk technique 2.1: trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C 3.1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / water; acetone / 16 h / 20 °C 3.2: 20 °C 4.1: sodium tetrahydroborate / diethyl ether; methanol / 20 °C View Scheme

(-)-di-tert-butyl [(1S)-1-methylprop-2-en-1-yl]imidodicarbonate (129076-07-9) → (S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C 2.1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / water; acetone / 16 h / 20 °C 2.2: 20 °C 3.1: sodium tetrahydroborate / diethyl ether; methanol / 20 °C View Scheme

(S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9) → Boc-Ala-H (79069-50-4)

Conditions	Yield
With water; Dess-Martin periodane In dichloromethane at 20℃; for 1h;	100%
Stage #1: (S)-2-t-butoxycarbonylaminopropan-1-ol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.25h; Stage #2: With triethylamine In dichloromethane at -78 - 0℃; for 0.583333h;	99%
With Dess-Martin periodane; tert-butyl alcohol In dichloromethane Ambient temperature;	97%

(S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9) + methanesulfonyl chloride (124-63-0) → (2S)-2-[(tert-butoxycarbonyl)amino]propyl methanesulfonate (126301-16-4)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 4h; Inert atmosphere;	100%
With triethylamine In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate	98.1%
With triethylamine In dichloromethane at 0 - 20℃; for 3h;	98%

(S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9) → tert-butyl (4S)-4-methyl-2-oxido-1,2,3-oxathiazolidin-2-ium-3-carboxylate (950852-76-3)

Conditions	Yield
With 1H-imidazole; thionyl chloride; triethylamine In dichloromethane at -50 - 0℃; for 4.5h;	100%
Stage #1: (S)-2-t-butoxycarbonylaminopropan-1-ol With 1H-imidazole; thionyl chloride; triethylamine Stage #2: In dichloromethane at 20℃;	100%
With 1H-imidazole; thionyl chloride; triethylamine In dichloromethane at -60 - -55℃; for 3.5h;	100%

(S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9) + N-(Benzyloxycarbonyl)glycine (1138-80-3) → (2S)-2-((tert-butoxycarbonyl)amino)propyl N-((benzyloxy)carbonyl)glycinate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride	100%
With dmap In N,N-dimethyl-formamide at 20℃;	10.45 g

(S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9) + tert-butyldimethylsilyl chloride (18162-48-6) → (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)propan-2-ylcarbamate (909297-88-7)

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃;	99%
With N-ethyl-N,N-diisopropylamine In dichloromethane for 1h;

(S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9) + methanesulfonyl chloride (124-63-0) → methanesulfonic acid 2-tert-butoxycarbonylamino-propyl ester (149602-63-1)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.5h;	98%

(S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9) + 5-bromo-1-(2,6-difluoro-benzyl)-6-methyl-1H-pyrimidine-2,4-dione (352303-66-3) → 5-bromo-1-(2,6-difluorobenzyl)-3-[2-(S)-N-Boc-aminopropyl]-6-methyluracil (675605-94-4)

Conditions	Yield
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h; Mitsunobu reaction;	96.1%
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran Mitsunobu reaction;
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction;
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran Mitsunobu reaction;

(S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9) + isobutyryl chloride (79-30-1) → [(2S)-2-aminopropyl] 2-methylpropanoate hydrochloride

Conditions	Yield
Stage #1: (S)-2-t-butoxycarbonylaminopropan-1-ol; isobutyryl chloride With dmap; triethylamine In dichloromethane at 0 - 20℃; Stage #2: With hydrogenchloride In 1,4-dioxane at 20℃; for 2h;	96%

phthalimide (136918-14-4) + (S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9) → (S)-tert-butyl (1-(1,3-dioxoisoindolin-2-yl)propan-2-yl)carbamate

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 16h;	92%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Mitsunobu reaction; Inert atmosphere;	69%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 25℃; for 3h;

Chloro-oxo-acetic acid (4732-69-8) + (S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9) → Boc-Ala-H (79069-50-4)

Conditions	Yield
With potassium hydrogensulfate; sodium hydrogencarbonate; triethylamine In hexane; dichloromethane; water	92%

(S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9) + acetyl chloride (75-36-5) → (S)-2-((tert-butoxycarbonyl)amino)propyl acetate

Conditions	Yield
With sodium carbonate In dichloromethane at 20℃; for 4h;	92%

(S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9) + 3-phenyl-1-(1H-pyrrol-1-yl)-1-propanone (112448-69-8) → C17H25NO4

Conditions	Yield
With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel (0) In toluene at 20℃; for 18h; Sealed tube; chemoselective reaction;	92%

(S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9) → tert-butyl N-[(1S)-2-iodo-1-methylethyl]carbamate (161529-20-0)

Conditions	Yield
With 1H-imidazole; polystyryl diphenyl phosphine-iodine In dichloromethane for 1h; Heating;	90%
With 1H-imidazole; diphenylphosphinopolystyrene; iodine In dichloromethane for 1h; Heating;	90%
With 1H-imidazole; iodine; triphenylphosphine In tetrahydrofuran at 20℃; for 10h; Inert atmosphere; Cooling;	89%

(S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9) + 7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid methyl ester (86788-49-0) → (S)-(-)-methyl 7-(2-(tertbutoxycarbonylamino)propoxy)-2-oxo-2H-chromone-3-carboxylate

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Mitsunobu Displacement;	90%

(S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9) → (S)-2-(methylamino)propan-1-ol hydrochloride (40916-61-8)

Conditions	Yield
Stage #1: (S)-2-t-butoxycarbonylaminopropan-1-ol With dibutylmagnesium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In n-heptane at 90℃; for 24h; Inert atmosphere; Stage #2: With hydrogenchloride In water; ethyl acetate for 0.25h;	90%

(S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9) → 1-azido-(S)-2-(N-tert-butoxycarbonyl)aminopropane (146610-69-7)

Conditions	Yield
With sodium azide; diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 70℃;	89%
Multi-step reaction with 2 steps 1: TEA / tetrahydrofuran / 0 °C 2: NaN3 / dimethylformamide / 55 - 60 °C View Scheme
Multi-step reaction with 2 steps 1: 82 percent / triethylamine / CH2Cl2 / 1.) 0 deg C, 30 min, 2.) RT, 30 min 2: 89 percent / sodium azide / hexamethylphosphoric acid triamide / 6 h / 55 °C View Scheme

(S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9) + 4-chlorobenzoyl chloride (586-75-4) → 4-Bromo-benzoic acid (S)-2-tert-butoxycarbonylamino-propyl ester (936494-89-2)

Conditions	Yield
With pyridine at 20℃; for 0.5h;	88%
With pyridine at 23℃;

(5Z)-5-({1-[4-chloro-2-(trifluoromethyl)benzyl]-1H-indazol-5-yl}methylidene)-2,4-dioxo-1,3-thiazolidine (1351564-76-5) + (S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9) → 3-[(2S)-2-(tertbutyloxycarbonyl)aminopropyl]-5-({1-[4-chloro-2-(trifluoromethyl)benzyl]-1H-indazol-5-yl}methylidene)-1,3-thiazolidine-2,4-dione

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu Displacement;	88%

(S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9) + p-toluenesulfonyl chloride (98-59-9) → (S)-O-(p-tolylsulfonyl)-N-(tert-butyloxycarbonyl)-1-hydroxy-2-aminopropane (84765-24-2)

Conditions	Yield
With pyridine at 4℃;	87%
In pyridine; dichloromethane	87%
In pyridine; dichloromethane	87%

NH-pyrazole (288-13-1) + (S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9) → (S)-(1-(1H-pyrazol-1-yl)propyl-2-yl)amino tert-butyl ester

Conditions	Yield
Stage #1: NH-pyrazole; (S)-2-t-butoxycarbonylaminopropan-1-ol With triphenylphosphine In ethyl acetate at 10℃; for 4h; Inert atmosphere; Stage #2: With di-isopropyl azodicarboxylate In ethyl acetate at 10 - 20℃; Inert atmosphere;	86.8%

(S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9) + N-2-nitrobenzenesulfonamideglycine methyl ester (215056-52-3) → [(2-tert-butoxycarbonylamino-propyl)-(2-nitro-benzenesulfonyl)-amino]-acetic acid methyl ester (380228-28-4)

Conditions	Yield
With dialkyl azodicarboxylate; triphenylphosphine In tetrahydrofuran Mitsunobu reaction;	86%

6-bromo-pyridin-3-ol (55717-45-8) + (S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9) → tert-butyl {(1S)-2-[(6-bromopyridin-3-yl)oxy]-1-methylethyl}carbamate (1380067-94-6)

Conditions	Yield
With azodicarboxylic acid bis(2-methoxyethyl) ester; triphenylphosphine In 1,4-dioxane at 60℃; for 1h;	86%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; toluene at 20℃; for 3h;

(S)-2-t-butoxycarbonylaminopropan-1-ol (79069-13-9) + thioacetic acid (507-09-5) → (S)-2-<(tert-Butoxycarbonyl)amino>propyl thioacetate (121920-47-6)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate	85%
Stage #1: (S)-2-t-butoxycarbonylaminopropan-1-ol With methanesulfonyl chloride; triethylamine In dichloromethane at 0 - 20℃; for 1h; Stage #2: tiolacetic acid With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	7.5 g

Upstream product

• 3744-87-4 Boc-(R)-Ala 
• 127407-54-9 (S)-2-t-butoxycarbonylamino-3-benzyloxy-1-methanesulfonyloxypropane 
• 2749-11-3 (S)-Alaninol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 115378-33-1 (-)-tert-butyl [(1S)-1-methylprop-2-en-1-yl]carbamate 
• 5856-62-2 (S)-2-aminobutan-1-ol 
• 51779-32-9 iminodicarboxylic acid di-tert-butyl ester 
• 129076-07-9 (-)-di-tert-butyl [(1S)-1-methylprop-2-en-1-yl]imidodicarbonate 
• 112392-66-2 methyl 2-{[(tert-butoxy)carbonyl]amino}propanoate 
• 28875-17-4 (S)-N-(tert-butoxycarbonyl)alanine methyl ester 
• 117049-08-8 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl<(tert-butoxycarbonyl)amino>bromoacetate 
• 4530-20-5 BOC-glycine 
• 117049-10-2 2-tert-Butoxycarbonylamino-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 6168-72-5 2-Amino-1-propanol 

Downstream Products

• 155768-90-4 2-[(R)-N-(tert-butyloxycarbonyl)amino]-1-phenoxypropane 
• 194156-54-2 tert-butyl (S)-(1-methoxypropan-2-yl)carbamate 
• 1297539-60-6 (S)-tert-butyl 1-(3-(3-chloro-4-cyano-2-methylphenyl)-1H-pyrazol-1-yl)propan-2-ylcarbamate 
• 1297537-41-7 (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile 
• 1315563-29-1 C₁₅H₂₃NO₃S 
• 1414377-85-7 (2R,3S)-tert-butyl 3-methylaziridine-2-carboxylate 
• 1429187-68-7 (R)-tert-butyl 1-(2,6-dichlorophenoxy)propan-2-yl carbamate 
• 1188301-70-3 (S)-tert-butyl 1-(4-(4-bromo-2-(4-trifluoromethyl)phenyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-5-yl)pyrimidin-2-ylamino)propan-2-ylcarbamate 
• 1452466-25-9 {(2S)-1-[({[(2S,5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]propan-2-yl}carbamic acid tert-butyl ester 
• 1431532-81-8 tert-butyl ((2S)-1-(3-((4-(cyclopropylmethoxy)benzoyl)amino)-4-nitrophenoxy)propan-2-yl)carbamate 
• 1431532-82-9 tert-butyl ((2S)-1-((2-(4-(cyclopropylmethoxy)phenyl)-1H-benzimidazol-6-yl)oxy)propan-2-yl)carbamate 
• 1431534-54-1 tert-butyl ((2S)-1-((5-((4-(cyclopropylmethoxy)-2,6-dimethylbenzoyl)amino)-4-hydroxypyridin-2-yl)oxy)propan-2-yl)carbamate 
• 1431532-80-7 tert-butyl ((2S)-1-(3-amino-4-nitrophenoxy)propan-2-yl)carbamate 
• 149632-73-5 dl-1-amino-2-(1,1-dimethylethoxy)carbonylamino-propane 

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Thiamin hydrochloride promoted highly efficient and ecofriendly approach has been described for the chemoselective N-tert-butyloxycarbonylation of amines under solvent-free conditions at ambient temperature. The demonstrated approach has been applicable for the N-Boc protection of variety of aliphatic, aryl, heteroaryl amines. The chemoselective protection of amino group occurs in chiral amines and amino alcohol without racemization in high yield. Thiamin hydrochloride is stable, economical, easy to handle and environmentally friendly.

Sulfated tungstate: A highly efficient, recyclable and ecofriendly catalyst for chemoselective N-tert butyloxycarbonylation of amines under the solvent-free conditions

Sulfated tungstate catalyzed an efficient and ecofriendly protocol has been described for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions at room temperature. The variety of functionalized aliphatic, aromatic and heteroaromatic amines efficiently undergoes the N-tert-butyloxycarbonylation under the developed protocol. The aminoalcohol, aminophenol, aminoester as well as various chiral amines underwent the chemoselective N-Boc protection under the optimized reaction condition. The rapid reaction rate, mild conditions, very good functional group tolerance, excellent yield, solvent-free, easy recovery products and excellent catalyst recyclability are the advantages of this protocol. This makes the protocol feasible, economical and environmentally benign.