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CAS No. : | 102520-97-8 | MDL No. : | MFCD03788641 |
Formula : | C9H19NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SBWYTQQSTIUXOP-UHFFFAOYSA-N |
M.W : | 189.25 | Pubchem ID : | 14578673 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.89 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 51.09 |
TPSA : | 58.56 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.84 cm/s |
Log Po/w (iLOGP) : | 2.39 |
Log Po/w (XLOGP3) : | 0.86 |
Log Po/w (WLOGP) : | 1.28 |
Log Po/w (MLOGP) : | 0.95 |
Log Po/w (SILICOS-IT) : | 0.46 |
Consensus Log Po/w : | 1.19 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.23 |
Solubility : | 11.3 mg/ml ; 0.0595 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.67 |
Solubility : | 4.01 mg/ml ; 0.0212 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.49 |
Solubility : | 6.18 mg/ml ; 0.0327 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.21 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With ruthenium(IV) oxide; sodium periodate In tetrachloromethane; water; acetonitrile at 20℃; for 2 h; | General procedure: To a solution of N-protected amino alcohol 4a–g (0.5 mmol) in a 2:2:3 mixture of CCl4/MeCN/H2O (7 mL) were successively added NaIO4(321 mg, 1.5 mmol) and RuO2·xH2O (3.5 mg, 0.025 mmol) at r.t. Theresulting dark mixture was vigorously stirred for 2 h at r.t. thenCH2Cl2 (10 mL) and H2O (10 mL) were added. The layers were separatedand the aqueous phase was extracted with CH2Cl2 (2 × 10 mL). Thecombined organic layers were washed with brine, dried over MgSO4,filtered and the solvent was removed in vacuo. The black residue waspurified by chromatography on silica gel (CH2Cl2–MeOH, 99:1 to95:5) to afford the N-Boc-protected amino acid 7a–g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 90℃; Inert atmosphere Stage #2: With water; sodium hydroxide In tetrahydrofuran at 0℃; for 1 h; |
D16 (b) 2-methyl-2-(methylamino)propan-l-ol HNL A solution of tert-butyl(l-hydroxy-2-methylpropan-2-yl)carbamate (67 g, 354 mmol) in tetrahydrofuran (THF) (150 mL) was added dropwise to a stirred solution of LiAlH4 (40.3 g, 1062 mmol) in tetrahydrofuran (THF) (400 mL) under nitrogen at 0 °C with stirring. The reaction mixture was stirred at 90 °C overnight, cooled, and then quenched by adding water (40.5 mL) at 0 °C. Then aqueous NaOH (15percent, 40.5 mL) was added dropwise followed by adding water (40.5 mL). The mixture was stirred for 1 h, and then filtered through ceilite. The organic layer was dried over sodium sulphate, and then concentrated in vacuo to afford the title compound (28 g, 77percent) without further purification. LC-MS (ESI): m/z 104 [M + H]+; 0.24 min (ret time). |
200 g | With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 18 h; Inert atmosphere; Reflux | Intermediate 13: 2-methyl-2-(methylamino ropan-l-ol To a stirred mixture of lithium aluminium hydride (301 g, 7.93 mol) in THF (5 L) under nitrogen in at 0 QC was added a solution of ieri-butyl (l-hydroxy-2-methylpropan-2-yl) carbamate (500 g, 2.62 mol) in THF (1 L) drop wise. The reaction mixture was stirred under reflux for 18 h. The reaction mixture was quenched with saturated Na2S04 solution (600 mL) and filtered through a Celite bed, dried over anhydrous Na2S04 and concentrated under reduced pressure to afford the title compound (200g) as a yellow solid. (0253) H NM (300 MHz, DMSO-d6) δ: 4.41 (1H, bs), 3.13 (2H, s), 2.14 (3H, s), 1.11 (1H, s), 0.89 (6H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triethylamine In dichloromethane at 20℃; for 2.83333 h; | (3a) (2-Hydroxy-1,1-dimethylethyl)carbamic acid t-butyl ester 230.4 ml of di-t-butyl dicarbonate (1.00 mol) was added to a solution of 98.05 g of 2-amino-2-methyl-1-propanol (1.10 mol) and 154 ml of triethylamine (1.10 mol) in methylene chloride (500 ml) at room temperature over 20 minutes, and the mixture was stirred at room temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure and diluted with a 10percent citric acid aqueous solution, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure to obtain 189.25 g of the crude title compound (yield: quant.). Colorless solid. 1H NMR spectrum (CDCl3, 400 MHz), δ: 4.64 (br s, 1H), 4.01 (br s, 1H), 3.59 (d, 2H, J = 6.3 Hz), 1.43 (s, 9H), 1.25 (s, 6H). |
99% | With iron(III) trifluoromethanesulfonate In neat (no solvent) at 20℃; for 0.0666667 h; Green chemistry | General procedure: Fe(OTf)3 (1 molpercent) was added to a magnetically stirred mixture of anamine (1 mmol) and Boc2O (1 mmol) at room temperature. The mixturewas stirred until completion of the reaction (TLC), then diluted withEtOAc and washed with water. The organic layer was dried overanhydrous MgSO4, then the solvent was distillated off under vacuum toyield the highly pure N‑Boc derivatives |
98% | at 0 - 20℃; for 2 h; | Di-tert-butyl dicarbonate (21.82 g, 100.00 mmol) was added in portions to a solution of 2- amino-2-methylpropan-i-ol (8.91 g, 100.0 mmol) in DCM (270 ml) at 0 °C. The reaction was stirred at room temperature for 2 hours, then was washed with 2N HC1 (100 mL). The organic phase was dried (MgSO4) and concentrated in vacuo to give tert-butyl (1-hydroxy- 2-methylpropan-2-yl)carbamate (18.56 g, 98 percent) as a white solid. ‘H NMR (400 MHz,CDC13, 27 °C) 1.25 (6H, s), 1.43 (9H, s), 3.58 (2H, d), 4.67 (1H, s). |
97% | With triethylamine In dichloromethane at 22 - 25℃; for 4 h; | 2-Amino-2-methyl-l-propanol (5 g, 56.1 mmol), (Boc)20 (13.46 g, 61.7 mmol) and triethyl amine (6.24 g, 61.7 mmol) were dissolved in 50 mL of dichloromethane. The reaction mixture was stirred for 4 h at 22 to 25 °C. Above mixture was washed with water (25 mL x 2), dried over anhydrous sodium sulfate and concentrated under vacuum to get tert-buty] (1- hydroxy-2-methylpropan-2-yl)carbamate (10.3 g, 97percent yield). |
90% | With 1,3-disulfonic acid imidazolium hydrogen sulfate In neat (no solvent) at 20℃; for 0.0333333 h; Green chemistry | General procedure: Amine (1 mmol) was added to the mixture of (Boc)2O (1 mmol) and DSIMHS (6.5 mg, ~ 0.02 mmol) with constant stirring at room temperature under solvent-free conditions. After completion of the reaction (monitored by TLC), ethyl acetate (3 × 5 mL) was added to the reaction mixture and the catalyst was decanted and washed with ethyl acetate (2 × 5 mL) and dried. The product was purified by column chromatography, using ethyl acetate–petroleum ether (2:8) eluent. |
75.36% | With triethylamine In dichloromethane at 0 - 20℃; for 1 h; | To a solution of compound 1 (10.00 g, 112.18 mmol, 1.00 Eq) in DCM (200 mL) was added Et3N (23.00 g, 227.30 mmol, 2.03 Eq). The mixture was cooled to 0° C. and Boc2O (38.40 g, 175.95 mmol, 1.57 Eq) was added, the mixture was stirred at 20° C. for 1 hr. The mixture was diluted with EA and washed with water. The organic phase was concentrated in vacuo. The residue was purified by silica gel chromatography (Petroleum ether/Ethyl acetate=15/1) to afford compound 2 (16.00 g, 84.54 mmol, 75.36percent yield) as white solid. |
75.36% | With triethylamine In dichloromethane at 0 - 20℃; for 0.5 h; | To a solution of compound 1 (10.00 g, 112.18 mmol, 1.00 Eq) in DCM (200 mL) was added Et3N (23.00 g, 227.30 mmol, 2.03 Eq). The mixture was cooled to 0° C. and Boc2O (38.40 g, 175.95 mmol, 1.57 Eq) was added, the mixture was stirred at 20° C. for 1 hr. The mixture was diluted with EA and washed with water. The organic phase was concentrated in vacuo. The residue was purified by silica gel chromatography (Petroleum ether/Ethyl acetate=15/1) to afford compound 2 (16.00 g, 84.54 mmol, 75.36percent yield) as white solid. |
68% | at 20℃; | Example 4 (tert-Butoxy)-N-(1-hydroxy-2-methylpropyl)carboxamide (4) Following the general procedure for the N-Boc-protection of ω-amino-2,2-dimethylalcohols of Description 2, 1.783 g (20.0 mmol) of 2-amino-2-methyl-1-propanol was reacted with 3.274 g (15.0 mmol) of di-tert-butyl-dicarbonate in a mixture of 20 mL of a saturated aqueous solution of sodium bicarbonate (NaHCO3) and 40 mL of acetonitrile to provide 1.937 g (68percent yield) of the title compound (4) as a colorless solid of sufficient purity to be used in subsequent steps without further isolation and purification. 1H NMR (400 MHz, CDCl3): δ=1.26 (s, 6H), 1.44 (s, 9H), 3.59 (d, J=6.0 Hz, 2H), 4.00-4.20 (br. m, 1H), 4.64-4.72 (br. m, 1H) ppm. MS (ESI) m/z 212.92 (M+Na)+. |
53% | at 25℃; for 1 h; | 2-Amino-2-methyl-propan-1-ol (53 g, 0.59 mol) and di-tert-butyl dicarbonate (65.0 g, 0.297 mol) were combined in H2O (500 mL) and stirred at 25 °C for 1 h. The reaction mixture was extracted with CHCl3 (2 x 250 mL). The organics were dried and concentrated to a white amorphous solid which was recrystallized from hot hexanes to afford desired material (30 g, 53percent) as a white solid: 13C NMR (CD3OD, 100 MHz) δ 157.76, 80.135, 70.095, 54.992, 29.247, 24.695. |
750 g | With sodium hydrogencarbonate; sodium carbonate In tetrahydrofuran; water at 0 - 20℃; for 18 h; | Intermediate 12: tert-butyl (l-hydroxy-2-meth lpropan-2-yl)carbamate - Preparation 2 To a solution of 2-amino-2-methylpropan-l-ol (500 g, 5.61 mol, Alfa) in THF (3.0 L) and water (1.0 L) was added Na2C03 (10.11 g, 95 mmol) and sodium bicarbonate (10.37 g, 123 mmol) and stirring continued at 0 QC. di-ferf-Butyl dicarbonate (1.56 L, 6.7 mol) was added. The reaction mixture was stirred at RT for 18 h. The THF layer was separated and the aqueous layer extracted with ethyl acetate (1.5 L). The combined organic layers were washed with brine solution (2 x 2 L), were dried over anhydrous Na2S04 and then concentrated under reduced pressure to afford crude title compound. The crude material was dissolved in petroleum ether (750 mL) and cooled to -50 °C. The resulting solid was filtered and washed with petroleum ether to give the title compound (750 g) as a white solid. (0250) *H NMR (400 MHz, DMSO-d6) δ: 6.08 (1H, s), 4.67 (1H, t), 3.29 (2H, s), 1.37 (9H, s), 1.13 (6H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | Stage #1: With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.5 h; Stage #2: With sodium hypochlorite In dichloromethane; water at 0℃; for 1.83333 h; |
(3b) (1,1-Dimethyl-2-oxoethyl)carbamic acid t-butyl ester 0.94 g of tetramethylpiperidine N-oxide (6.0 mmol) and 3.57 g of potassium bromide (30 mmol) were added to a solution of 56.78 g of (2-hydroxy-1,1-dimethylethyl)carbamic acid t-butyl ester obtained in Reference Example (3a) (300 mmol) in a mixture of methylene chloride (500 ml) and a saturated sodium bicarbonate aqueous solution (525 ml) under ice-cooling, and the mixture was stirred at the same temperature for 30 minutes. 534 ml of a 5percent sodium hypochlorite aqueous solution (360 mmol) was added to the reaction mixture under ice-cooling over 1.5 hours, and the mixture was stirred at the same temperature for 20 minutes. A saturated sodium thiosulfate aqueous solution was added to the reaction mixture, and the reaction mixture was returned to room temperature, followed by extraction with methylene chloride. Then, the organic layer was washed with brine and then dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. Hexane was added to the residue, and the solid was collected by filtration to obtain 42.32 g of the title compound (yield: 79percent). Colorless solid. 1H NMR spectrum (CDCl3, 400 MHz), δ: 9.43 (s, 1H), 4.97 (br s, 1H), 1.44 (s, 9H), 1.33 (s, 6H). |
71% | With triethylamine In dimethyl sulfoxide | B (1,1-Dimethyl-2-oxo-ethyl)-carbamic Acid Tert-Butyl Ester (2-Hydroxy-1,1-dimethyl-ethyl)-carbamic acid tert-butyl ester (11.3 g, 0.06 mol) and triethylamine (18.2 g, 0.18 mol) in DMSO (180 mL) at 25° C. was treated with a solution of pyridine-sulfurtrioxide complex (28.6 g, 0.18 mol) in DMSO (150 mL). The resulting mixture was stirred for 0.5 h, poured into H2O (100 mL) and extracted with ether (3*100 mL). The organics were washed with 10percent citric acid(aq) (250 mL), saturated NaHCO3 (250 mL) and then with brine (2*250 mL). The organics were dried and concentrated to an off-white solid which was recrystallized from hexanes to afford the desired material (8.0 g, 71percent) as white needles: 13C NMR (DMSO-d6, 100 MHz) δ 202.07, 155.58, 78.95, 58.64, 28.42, 21.58. |
71% | at 25℃; for 0.5 h; | (2-Hydroxy-1,1-dimethyl-ethyl)-carbamic acid tert-butyl ester (11.3 g, 0.06 mol) and triethylamine (18.2 g, 0.18 mol) in DMSO (180 mL) at 25 °C was treated with a solution of pyridine-sulfurtrioxide complex (28.6 g, 0.18 mol) in DMSO (150 mL). The resulting mixture was stirred for 0.5 h, poured into H2O (100 mL) and extracted with ether (3 x 100 mL). The organics were washed with 10percent citric acid (250 mL), saturated NaHCO3 (250 mL) and then with brine (2 x 250 mL). The organics were dried and concentrated to an off-white solid which was recrystallized from hexanes to afford the desired material (8.0 g, 71 percent) as white needles: 13C NMR (DMSO-d6, 100 MHz) δ 202.07, 155.58, 78.95, 58.64, 28.42, 21.58. |
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