Home Cart 0 Sign in  
X

[ CAS No. 39895-56-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 39895-56-2
Chemical Structure| 39895-56-2
Chemical Structure| 39895-56-2
Structure of 39895-56-2 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 39895-56-2 ]

Related Doc. of [ 39895-56-2 ]

Alternatived Products of [ 39895-56-2 ]

Product Details of [ 39895-56-2 ]

CAS No. :39895-56-2 MDL No. :MFCD06213766
Formula : C8H11NO Boiling Point : -
Linear Structure Formula :- InChI Key :WMOUKOAUAFESMR-UHFFFAOYSA-N
M.W : 137.18 Pubchem ID :6496943
Synonyms :

Calculated chemistry of [ 39895-56-2 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 40.24
TPSA : 46.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.53
Log Po/w (XLOGP3) : 0.21
Log Po/w (WLOGP) : 0.33
Log Po/w (MLOGP) : 0.94
Log Po/w (SILICOS-IT) : 1.28
Consensus Log Po/w : 0.86

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.13
Solubility : 10.1 mg/ml ; 0.0733 mol/l
Class : Very soluble
Log S (Ali) : -0.74
Solubility : 24.9 mg/ml ; 0.182 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.24
Solubility : 0.784 mg/ml ; 0.00571 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 39895-56-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 39895-56-2 ]

* 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.

  • Upstream synthesis route of [ 39895-56-2 ]
  • Downstream synthetic route of [ 39895-56-2 ]

[ 39895-56-2 ] Synthesis Path-Upstream   1~29

  • 1
  • [ 39895-56-2 ]
  • [ 874-89-5 ]
Reference: [1] Chemical Communications, 2001, # 5, p. 461 - 462
  • 2
  • [ 105-07-7 ]
  • [ 228546-60-9 ]
  • [ 589-18-4 ]
  • [ 874-89-5 ]
  • [ 39895-56-2 ]
Reference: [1] Chemical Communications, 2005, # 1, p. 40 - 42
  • 3
  • [ 874-89-5 ]
  • [ 39895-56-2 ]
YieldReaction ConditionsOperation in experiment
98% With ammonia; hydrogen In methanol for 20 h; (4-Aminomethyl-phenyl)-methanol hydrochloride salt 4-Hydroxymethyl-benzonitrile (2.0 g, 15 mol) was reduced using Raney nickel (0. 5g) and hydrogen (50 psi) in MeOH: NH3 (100ml) for 20 hours. The reaction mixture was filtered through a pad of celite. The filtrate was concentrated under reduced pressure to afford (4-aminomethyl-phenyl)-methanol hydrochloride salt (2.01 g, 98percent) as a white solid of sufficient purity for use without further purification: MS (APCI+) : m/z 138.3 (M+H); H-NMR (DMSO-d6) 8 7.20 (s, 4 H), 5.04 (s, 2 H), 4.42 (s, 2 H), 3.83 (s, 1 H), 2.45 (s, 2 H).
29% With lithium aluminium tetrahydride In diethyl ether at 0℃; for 3.25 h; Reflux Example 99
N-((4-(hydroxymethyl)phenyl)methyl)-N-(1-methylpiperidin-4-yl)-2-(4-methoxyphenyl)acetamide hydrochloride (57MBT72D)
To a stirred suspension of LiAlH4 (285 mg, 7.52 mmol) in diethylether (10 mL) at 0° C. was added a solution of 4-cyanobenzyl alcohol (0.5 g, 3.76 mmol) in diethylether (5 mL) over 15 min.
The grey reaction mixture was heated to reflux for 3 h.
After cooling to r.t., the mixture was treated successively with water (1 mL), 2M NaOH (2 mL) and water (2 mL) under vigorous stirring.
The resulting white slurry was filtered and washed with CH2Cl2 (20 mL).
Extraction with additional CH2Cl2 (20 mL) and n-butanol (20 mL) and evaporation yielded an oil, which upon flash chromatography (0-15percent MeOH in CH2Cl2) gave 152 mg (29percent) of 4-(aminomethyl)benzylalcohol (57MBT52B) as a white solid. Rf=0.51 (30percent MeOH in CH2Cl2+3.5percent NH4OH).
29%
Stage #1: With lithium aluminium tetrahydride In diethyl ether at 0℃; for 3.25 h; Heating / reflux
Stage #2: With sodium hydroxide In diethyl ether; water at 20℃;
To a stirred suspension of LiAlHU (285 mg, 7.52 mmol) in diethylether (10 mL)at 0° C. was added a solution of 4-cyanobenzyl alcohol (0.5 g, 3.76 mmol) in diethylether (5 mL) over 15 min. The grey reaction mixture was heated to reflux for 3 h. After cooling to r.t, the mixture was treated successively with water (1 mL), 2M NaOH (2 mL) and water (2 mL) under vigorous stirring. The resulting white slurry was filtered and washed with CH2Cl2 (20 mL). Extraction with additional CH2Cl2 (20 mL) and n- butanol (20 mL) and evaporation yielded an oil, which upon flash chromatography (0- 15percent MeOH in CH2Cl2) gave 152 mg (29percent)of 4-(aminomethyl)benzylalcohol (57MBT52B) as a white solid. Rf=0.51 (30percent MeOH in CH2Cl2 +3.5percent NH4 OH).
Reference: [1] Patent: WO2005/56004, 2005, A1, . Location in patent: Page/Page column 154-155
[2] ACS Catalysis, 2018, vol. 8, # 10, p. 9125 - 9130
[3] Journal of Organic Chemistry, 1998, vol. 63, # 22, p. 7663 - 7669
[4] Patent: US2015/259291, 2015, A1, . Location in patent: Paragraph 0612
[5] Patent: WO2007/124136, 2007, A1, . Location in patent: Page/Page column 130
[6] Organic Mass Spectrometry, 1990, vol. 25, # 12, p. 649 - 654
[7] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 9, p. 3187 - 3200
[8] Chemical Communications, 2010, vol. 46, # 7, p. 1073 - 1075
[9] Journal of Medicinal Chemistry, 2009, vol. 52, # 1, p. 33 - 47
[10] Journal of Medicinal Chemistry, 2014, vol. 57, # 19, p. 8140 - 8151
  • 4
  • [ 1129-35-7 ]
  • [ 39895-56-2 ]
YieldReaction ConditionsOperation in experiment
80% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 50℃; for 15 h; To a suspension of lithium aluminium hydride in tetrahydrofuran (400 mL) stirred in air at 0 °C was added a solution of methyl 4-cyanobenzoate (10 g, 62.1 mmol) in tetrahydrofuran (400 mL) dropwise over 15 minutes. The reaction mixture was stirred at 50 °C for 15 hours and then cooled to 0°C and quenched by the slow addition of water (7 mL), 15percent NaOH (7 mL), and water (21 mL). The resulting precipitate was stirred for an additional 30 minutes and filtered. The filtrated was concentrated in vacuo to give (4- (aminomethyl)phenyl)methanol (6.8 g, 80percent yield) as a light yellow oil. LCMS m/z = 138.0 [M+H]+.
Reference: [1] Patent: WO2017/216726, 2017, A1, . Location in patent: Page/Page column 941
[2] Journal of the American Chemical Society, 2004, vol. 126, # 15, p. 4762 - 4763
[3] Journal of Agricultural and Food Chemistry, 2013, vol. 61, # 37, p. 8730 - 8736
[4] Tetrahedron, 2011, vol. 67, # 12, p. 2251 - 2259
  • 5
  • [ 56-91-7 ]
  • [ 39895-56-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 13, p. 5719 - 5732
[2] Chemistry - A European Journal, 2012, vol. 18, # 5, p. 1383 - 1400
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 10, p. 3165 - 3168
[4] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 1, p. 161 - 175
[5] Patent: EP748310, 1999, B1,
[6] Patent: US5827881, 1998, A,
[7] Angewandte Chemie - International Edition, 2010, vol. 49, # 37, p. 6633 - 6637
[8] Steroids, 2012, vol. 77, # 12, p. 1177 - 1191,15
[9] Steroids, 2012, vol. 77, # 12, p. 1177 - 1191
[10] Journal of Medicinal Chemistry, 2012, vol. 55, # 23, p. 10460 - 10474
[11] Patent: WO2013/109859, 2013, A1, . Location in patent: Paragraph 0298
[12] RSC Advances, 2013, vol. 3, # 38, p. 17150 - 17155
[13] Patent: WO2017/100154, 2017, A1, . Location in patent: Paragraph 00120
  • 6
  • [ 439691-96-0 ]
  • [ 39895-56-2 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With triphenylphosphine In tetrahydrofuran at 60℃; for 1 h;
Stage #2: With water In tetrahydrofuranHeating
1.6 l-(Aminomethyl)-4-(hydroxymethyl)benzene, 6.6Azide 5 (1.96 g, 12.0 mmol) and PPh3 (6.50g, 24.8 mmol, 2.05 eq) were dissolved in THF (25 ml) and heated at 60°C for ] hour. Water (4.5 ml, 248 mmol, 20 eq) was added and the reaction was heated overnight. The solvent was evaporated and the reidue obtained was purified by flash chromatography (eluent DCM to 4: 1 DCM / methanol saturated with NH3) to yield 6 as a white solid (1.44 g, 10.5 mmol, 85percent). Rf = 0.05 (9:1, DCM / MeOH sat. NH3); vmax = cm"1; NMR (300 MHz, CDC13) δ = 7.35 (d, 3J(H,H) = 8.4 Hz, 2H, ArCH a to CH2NH2), 7.30 (d, 3J(H,H) = 8.4 Hz, 2H, ArCH a to C3/4OH), 4.67 (s, 2H, G3/4OH), 3.85 (s, 2H, CH2NH2), 1 68 (bs, 3H, OH NH2); C NMR (75 MHz, CDCI3) δ = 142.6 (ArCCH2NH2), 139.6 (ArCC3/4OH), 127.3 (ArCH), 127.2 (ArCH), 65.0 (CH2OH), 46.2 (CH2N3/4); HRMS (ESI+): m/z calculated for C8Hi2NO [M + H : 138.0913, found 138.0933.
Reference: [1] Patent: WO2012/95628, 2012, A1, . Location in patent: Page/Page column 17-18
  • 7
  • [ 105-07-7 ]
  • [ 39895-56-2 ]
YieldReaction ConditionsOperation in experiment
73% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; To a cooled suspension of lithium aluminu 3 mmol) in tetrahydrofuran (50 mL) at 0 °C was added a solution of 4-formylbenzonitrile (5 g, 38.1 mmol) in tetrahydrofuran (50 mL). The resultant mixture was stirred at room temperature overnight then recooled to 0 °C and treated with a solution of aqueous sodium hydroxide solution (5 N, 32.1 mL). The resultant mixture was then filtrated and the filtrate concentrated in vacuo to provide (4-(aminomethyl)phenyl)methanol (4.5 g, 73 percent) as a white solid. LCMS m/z = 138.1 [M+H]+.
Reference: [1] Chemical Science, 2017, vol. 8, # 12, p. 7947 - 7953
[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 3116 - 3126
[3] Angewandte Chemie - International Edition, 2012, vol. 51, # 4, p. 941 - 944
[4] RSC Advances, 2014, vol. 4, # 63, p. 33564 - 33568
[5] Journal of the American Chemical Society, 2011, vol. 133, # 17, p. 6745 - 6751
[6] Journal of Organic Chemistry, 2009, vol. 74, # 5, p. 1964 - 1970
[7] Patent: WO2017/216726, 2017, A1, . Location in patent: Page/Page column 618; 621
[8] European Journal of Organic Chemistry, 2008, # 36, p. 6144 - 6151
[9] ChemCatChem, 2013, vol. 5, # 1, p. 322 - 330
[10] Journal of Medicinal Chemistry, 2013, vol. 56, # 12, p. 5198 - 5202
[11] Organic Letters, 2013, vol. 15, # 22, p. 5870 - 5873
[12] Angewandte Chemie - International Edition, 2014, vol. 53, # 26, p. 6720 - 6723[13] Angew. Chem., 2014, vol. 126, # 26, p. 6838 - 6841,4
[14] Chemical Communications, 2017, vol. 53, # 48, p. 6448 - 6451
  • 8
  • [ 6232-11-7 ]
  • [ 39895-56-2 ]
Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 15, p. 4786 - 4797
[2] Patent: EP1550657, 2005, A1, . Location in patent: Page/Page column 48
[3] Patent: EP1724263, 2006, A1, . Location in patent: Page/Page column 16
  • 9
  • [ 79606-51-2 ]
  • [ 39895-56-2 ]
  • [ 122-39-4 ]
Reference: [1] ACS Catalysis, 2016, vol. 6, # 10, p. 6377 - 6383
  • 10
  • [ 17201-43-3 ]
  • [ 39895-56-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 9, p. 3187 - 3200
[2] Journal of Organic Chemistry, 1998, vol. 63, # 22, p. 7663 - 7669
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 19, p. 8140 - 8151
  • 11
  • [ 6757-31-9 ]
  • [ 39895-56-2 ]
Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 672,674
  • 12
  • [ 1679-64-7 ]
  • [ 39895-56-2 ]
Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 672,674
  • 13
  • [ 168761-51-1 ]
  • [ 182963-64-0 ]
  • [ 39895-56-2 ]
Reference: [1] Patent: US5698560, 1997, A,
  • 14
  • [ 125734-44-3 ]
  • [ 39895-56-2 ]
Reference: [1] Patent: WO2012/95628, 2012, A1,
  • 15
  • [ 81172-89-6 ]
  • [ 39895-56-2 ]
Reference: [1] Patent: WO2012/95628, 2012, A1,
  • 16
  • [ 51359-78-5 ]
  • [ 39895-56-2 ]
Reference: [1] Patent: WO2012/95628, 2012, A1,
  • 17
  • [ 52010-97-6 ]
  • [ 39895-56-2 ]
Reference: [1] Patent: WO2012/95628, 2012, A1,
  • 18
  • [ 510772-10-8 ]
  • [ 39895-56-2 ]
Reference: [1] Patent: WO2012/95628, 2012, A1,
  • 19
  • [ 105-07-7 ]
  • [ 228546-60-9 ]
  • [ 589-18-4 ]
  • [ 874-89-5 ]
  • [ 39895-56-2 ]
Reference: [1] Chemical Communications, 2005, # 1, p. 40 - 42
  • 20
  • [ 7153-22-2 ]
  • [ 39895-56-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1959, vol. 628, p. 172,181
  • 21
  • [ 24424-99-5 ]
  • [ 39895-56-2 ]
  • [ 33233-67-9 ]
YieldReaction ConditionsOperation in experiment
97% With sodium hydrogencarbonate In tetrahydrofuran; water at 0℃; 4-Aminomethylbenzyl alcohol (1.0 g, 6.60 mmol) was slurried in a mixture of THF (10 mL) and water (10 ml_). A solution of saturated sodium hydrogen carbonate was added until the pH of the solution was > pH 9. The mixture was cooled to 0 0C and di- tert-butyldicarbonate (2.89 g, 13.23 mmol) added. The reaction was allowed to stir overnight then THF removed under vacuum. The aqueous mixture was extracted with EtOAc (20 mL) and then acidified to pH 3 by addition of 1 N HCI. This was extracted with EtOAc (2 x 10 mL), the organic layers combined, dried (MgSO4) and evaporated to dryness to afford the desired product (1.60 g, 97percent). m/z 252 [M++H]+
Reference: [1] Patent: WO2006/117549, 2006, A1, . Location in patent: Page/Page column 147
  • 22
  • [ 39895-56-2 ]
  • [ 42383-05-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 1, p. 161 - 175
  • 23
  • [ 24424-99-5 ]
  • [ 39895-56-2 ]
  • [ 123986-64-1 ]
YieldReaction ConditionsOperation in experiment
99% at 20℃; for 48 h; Boc2O was added in one portion at r.t. to a solution of (4-aminomethyl-phenyl)-methanol Compound 3a (21.2 mmol, 2.9 g) in CH2C12 (100 mL). The resulting solution wasstirred for 48h, then washed with a 10percent citric acid solution (50 mL) followed by brine. Theorganic layer was separated, then dried over Na2SC>4 and filtered. The solvent was removed invacua to obtain (4-hydroxymethyl-benzyl)-carbamic acid tert-butyl ester Compound 3b as awhite solid (5.2 g, 99percent yield), which was used in the next step without further purification.MnO2 (9.6 g) was added to a solution of Compound 3b (21.2 mmol, 5.2 g) inchloroform (60 mL), forming a black suspension that was stirred at r.t. overnight then filteredthrough a pad of celite. The solvent was evaporated in vacua to obtain (4-forinyl-benzyl)-carbamic acid tert-butyl ester Compound 3c as a white solid (4.3 g, 87percent yield), which was usedin the next step without purification.; NaB(OAc)3H (2.8 mmol, 0.58 g) was added to a mixture of Compound 3c (2.6 mmol,0.6 g) and tetrahydro-pyran-4-ylamine Compound 3d (2.6 mmol, 0.26 g) in CH2C12 (25 mL)and the resulting suspension was stirred at r.t. An aliquot of the reaction mixture showed theformation of product (MS m/e 321; 100percent). An aqueous solution of formaldehyde (37percentsolution, 8.6 mmol, 0.7 mL) was added to the reaction mixture, followed by NaB(OAc)3H (2.8mmol, 0.58 g) added in one portion under ice cooling. The reaction mixture was stirred at r.t.for about 2h, then made basic with a 2N NaOH solution and extracted with CH2C12. Theorganic layer was washed with brine, then separated and dried over Na2SO4. The drying agentwas filtered and the solvent was removed in vacua to yield (4-[methyl-(tetrahydro-pyran-4-yl)-amino]-methyl}-benzyl)-carbamic acid tert-butyl ester Compound 3e as a pale yellow oil.MS m/e 235 (M+H, 100percent). The product was purified by column chromatography (4:1CH2Cl2:MeOH) to yield a colorless oil (0.52 g, 59percent yield).; Compound 3e was dissolved in CH2Cl2, then HC1 in dioxane was added and themixture was stirred at r.t. for 12 hrs. The solvent was removed and the gummy residue wasmade basic with 2N NaOH and extracted with EtOAc. The organic layer was washed withbrine, then separated and dried over Na2SO4. The drying agent was filtered and the solvent wasremoved in vacua to obtain (4-aminomethyl-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amineCompound 3f as a pale yellow oil (0.3 g, 83percent yield). MS m/e 235 (M+H, 100percent).; A solution of 3-(3-trifluoromethyl-phenyl)-acryloyl chloride Compound 3g (0.3 mrnol,0.07 g) in THF (2 mL) was added dropwise to a solution of Compound 3f (0.2 mmol, 0.05 g)and Et3N (0.8 mmol, 0.14 mL) in THF (10 mL) at 0°C. The resulting suspension was allowedto warm to r.t. overnight. The reaction mixture was made basic with a 2N NaOH solution andextracted with EtOAc (25 mL). The aqueous layer was extracted with EtOAc (2X10 mL) andthe organic layers were washed with brine, then dried over Na2SO4 and filtered. The solventwas removed in vacua to yield a yellow solid (with methane) as the product. The crude productwas purified by preparative TLC (9:1 EtOAc-.MeOH, Rf = 0.2) to yield N-(4-[methyl-(tetrahydro-pyran-4-yi)-amino]-methyl}-benzyi)-3-(3-trifluoromethyl-phenyl)-acrylamideCompound 3h (0.06 g, 49percent yield). MS m/e 433 (M+H, 100percent).; Mel (0.08 mL, 1.28 mmol) was added dropwise to a solution of Compound 3h (0.07mmol, 0.03 g) in a mixture of acetone:acetonitrile (2 mL). The resulting solution was stirred atr.t. for 24h to provide a residue. The residue was washed with ether (2x 1 mL) and dried undera high vacuum to provide Compound 64 (0.04 g, 93percent yield) as an iodide salt. MS m/e 584(M+H, 100percent).
99% at 20℃; for 48 h; Boc2O was added in one portion at r.t. to a solution of (4-aminomethyl-phenyl)-methanol Compound 3a (21.2 mmol, 2.9 g) in CH2Cl2 (100 mL). The resulting solution was stirred for 48 h, then washed with a 10percent citric acid solution (50 mL) followed by brine. The organic-layer was separated, then dried over Na2SO4 and filtered. The solvent was removed in vacuo to obtain (4-hydroxymethyl-benzyl)-carbamic acid tert-butyl ester Compound 3b as a white solid (5.2 g, 99percent yield), which was used in the next step without further purification.
88% Inert atmosphere 1.7 l-'Butoxycarbonylaminomethyl-4-hydroxymethyl benzene, 7.7Amine 6 (1.44g, 10.5 mmol) was dissolved in CHCI3 (50 ml) and Boc20 (2.29 g, 10.5 mmol, 1 eq) was added slowly. The reaction was stirred under nitrogen overnight before the solvent was evaporated and the residue obtained was dissolved in ethyl acetate (50 ml). This solution was washed with a citric acid solution (3 * 50 ml), brine (50 ml), dried over Na2S04, and evaporated to yield 7 as a white solid (2.20 g, 9.2 mmol, 88 percent). Rf = 0.57 (DCM / MeOH sat. N3/4, 8:2); Vmax = cm-1; 'H NMR (300 MHz, CDC13) δ - 7.33 (d, 3J(H,H) = 8.2 Hz, 2H, ArCH a to CH2OH), 7.26 (d, J(H,H) = 8.2 Hz, 2H, ArCH a to CH2NHBoc), 4.86 (bs, 1H, NHBoc), 4.68 (s, 2Η, CH^OH), 4.30 (d, 3J(H,H) = 5.7 Hz, 2H, CH?NHBoc), 1.96 (bs, 1H, OH), 1.46 (s, 9Η, C(CH?)3); l 3C NMR (75 MHz, CDC13) δ = 155.9 (CO), 140.0 (ArCCH2OH), 138.3 (ArCCH2NHBoc), 127.6 (ArCH a to CH2NHBoc), 127.2 (ArCH a to CH2OH), 85.2 (C(CH3)3), 65.0 (C3/4OH), 44.4 (CH2NHBoc), 28.4 (C(C3/4)3); HRMS (ESI+): m/z calculated for C,3Hi9N03Na [M + Na]+ : 260.1257, found 260.1253.
31% at 20℃; The mixture of (4-(aminomethyl)phenyl)methanol (1 g, 7.29 mmol) and di-tert-butyl dicarbonate (1.59 g, 7.29 mmol) in dichloromethane (30 mL) was stirred at room temperature overnight then concentrated under reduced pressure and the crude product was added to a silica gel column and was eluted with dichloromethane:ethyl acetate (1:1) to give tert-butyl 4-(hydroxymethyl)benzylcarbamate (0.8 g, 2.28 mmol, 31percent yield) as a white solid.1H NMR (400 MHz, DMSO-d6) δ ppm 7.37 (s, 1H), 7.22 (dd, J = 27.8, 8.0 Hz, 4H), 5.13 (t, J = 5.7 Hz, 1H), 4.46 (d, J = 5.7 Hz, 2H), 4.10 (d, J = 6.1 Hz, 2H), 1.36 (s, 9H).

Reference: [1] Patent: WO2006/12135, 2006, A1, . Location in patent: Page/Page column 49-51
[2] Patent: US2006/293379, 2006, A1, . Location in patent: Page/Page column 63
[3] Angewandte Chemie - International Edition, 2012, vol. 51, # 4, p. 941 - 944
[4] Chemical Communications, 2010, vol. 46, # 7, p. 1073 - 1075
[5] Journal of Medicinal Chemistry, 2009, vol. 52, # 1, p. 33 - 47
[6] Patent: WO2012/95628, 2012, A1, . Location in patent: Page/Page column 18
[7] Patent: WO2017/216726, 2017, A1, . Location in patent: Page/Page column 621
[8] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 1, p. 161 - 175
[9] Tetrahedron, 2002, vol. 58, # 4, p. 741 - 755
[10] Journal of Medicinal Chemistry, 2013, vol. 56, # 12, p. 5198 - 5202
[11] Chemical Science, 2017, vol. 8, # 12, p. 7947 - 7953
  • 24
  • [ 39895-56-2 ]
  • [ 123986-64-1 ]
Reference: [1] Patent: WO2006/117549, 2006, A1,
  • 25
  • [ 39895-56-2 ]
  • [ 187283-17-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 9, p. 3187 - 3200
[2] Journal of Medicinal Chemistry, 2009, vol. 52, # 1, p. 33 - 47
[3] Chemical Science, 2017, vol. 8, # 12, p. 7947 - 7953
[4] Journal of Medicinal Chemistry, 2018, vol. 61, # 13, p. 5719 - 5732
[5] Patent: WO2006/117549, 2006, A1,
  • 26
  • [ 24424-99-5 ]
  • [ 39895-56-2 ]
  • [ 187283-17-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 19, p. 8140 - 8151
  • 27
  • [ 39895-56-2 ]
  • [ 156866-52-3 ]
Reference: [1] Tetrahedron, 2002, vol. 58, # 4, p. 741 - 755
[2] Patent: WO2012/95628, 2012, A1,
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 12, p. 5198 - 5202
[4] Patent: WO2006/117549, 2006, A1,
  • 28
  • [ 24424-99-5 ]
  • [ 39895-56-2 ]
  • [ 156866-52-3 ]
Reference: [1] RSC Advances, 2013, vol. 3, # 38, p. 17150 - 17155
  • 29
  • [ 39895-56-2 ]
  • [ 674799-96-3 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 27, p. 11153 - 11160
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 39895-56-2 ]

Aryls

Chemical Structure| 40896-62-6

[ 40896-62-6 ]

(3-(Aminomethyl)phenyl)methanol hydrochloride

Similarity: 0.97

Chemical Structure| 57685-24-2

[ 57685-24-2 ]

2-[(Methylamino)methyl]benzyl Alcohol

Similarity: 0.83

Chemical Structure| 5344-90-1

[ 5344-90-1 ]

(2-Aminophenyl)methanol

Similarity: 0.78

Chemical Structure| 73604-31-6

[ 73604-31-6 ]

3-Hydroxybenzylamine

Similarity: 0.77

Chemical Structure| 696-60-6

[ 696-60-6 ]

4-Hydroxybenzylamine

Similarity: 0.77

Alcohols

Chemical Structure| 40896-62-6

[ 40896-62-6 ]

(3-(Aminomethyl)phenyl)methanol hydrochloride

Similarity: 0.97

Chemical Structure| 57685-24-2

[ 57685-24-2 ]

2-[(Methylamino)methyl]benzyl Alcohol

Similarity: 0.83

Chemical Structure| 5344-90-1

[ 5344-90-1 ]

(2-Aminophenyl)methanol

Similarity: 0.78

Chemical Structure| 623-04-1

[ 623-04-1 ]

(4-Aminophenyl)methanol

Similarity: 0.76

Chemical Structure| 1877-77-6

[ 1877-77-6 ]

3-Aminobenzyl alcohol

Similarity: 0.76

Amines

Chemical Structure| 40896-62-6

[ 40896-62-6 ]

(3-(Aminomethyl)phenyl)methanol hydrochloride

Similarity: 0.97

Chemical Structure| 57685-24-2

[ 57685-24-2 ]

2-[(Methylamino)methyl]benzyl Alcohol

Similarity: 0.83

Chemical Structure| 5344-90-1

[ 5344-90-1 ]

(2-Aminophenyl)methanol

Similarity: 0.78

Chemical Structure| 73604-31-6

[ 73604-31-6 ]

3-Hydroxybenzylamine

Similarity: 0.77

Chemical Structure| 696-60-6

[ 696-60-6 ]

4-Hydroxybenzylamine

Similarity: 0.77