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Chemical Structure| 13325-10-5
Chemical Structure| 13325-10-5
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Product Details of [ 13325-10-5 ]

CAS No. :13325-10-5 MDL No. :MFCD00008230
Formula : C4H11NO Boiling Point : -
Linear Structure Formula :- InChI Key :BLFRQYKZFKYQLO-UHFFFAOYSA-N
M.W : 89.14 Pubchem ID :25868
Synonyms :
4-Amino-1-butanol

Calculated chemistry of [ 13325-10-5 ]

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 25.21
TPSA : 46.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.16 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.17
Log Po/w (XLOGP3) : -0.44
Log Po/w (WLOGP) : -0.28
Log Po/w (MLOGP) : -0.18
Log Po/w (SILICOS-IT) : -0.26
Consensus Log Po/w : 0.0

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.08
Solubility : 108.0 mg/ml ; 1.21 mol/l
Class : Highly soluble
Log S (Ali) : -0.07
Solubility : 76.6 mg/ml ; 0.859 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.47
Solubility : 30.5 mg/ml ; 0.342 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 13325-10-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:2735
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 13325-10-5 ]

* 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 [ 13325-10-5 ]
  • Downstream synthetic route of [ 13325-10-5 ]

[ 13325-10-5 ] Synthesis Path-Upstream   1~38

  • 1
  • [ 110-87-2 ]
  • [ 13325-10-5 ]
  • [ 16133-25-8 ]
  • [ 173843-37-3 ]
Reference: [1] Patent: US5760054, 1998, A,
  • 2
  • [ 110-63-4 ]
  • [ 13325-10-5 ]
Reference: [1] Patent: US2012/232309, 2012, A1, . Location in patent: Page/Page column 14-15; 16
[2] Patent: US2012/232294, 2012, A1, . Location in patent: Page/Page column 13-14; 15
[3] Patent: US2012/232292, 2012, A1, . Location in patent: Page/Page column 10; 12
[4] Patent: CN103502199, 2016, B, . Location in patent: Paragraph 0265; 0266
[5] Patent: JP2016/27052, 2016, A, . Location in patent: Paragraph 0088; 0095
[6] Patent: CN103502212, 2016, B, . Location in patent: Paragraph 0207-0208; 0212
  • 3
  • [ 110-63-4 ]
  • [ 123-75-1 ]
  • [ 5724-81-2 ]
  • [ 13325-10-5 ]
  • [ 110-60-1 ]
Reference: [1] Patent: US2012/232293, 2012, A1, . Location in patent: Page/Page column 12; 13
[2] Patent: US2012/232293, 2012, A1, . Location in patent: Page/Page column 12; 13
[3] Patent: CN103502199, 2016, B, . Location in patent: Paragraph 0265; 0266
[4] Patent: JP5808437, 2015, B2, . Location in patent: Paragraph 0099; 0106; 0107
[5] Patent: JP2016/27052, 2016, A, . Location in patent: Paragraph 0088; 0097
  • 4
  • [ 110-63-4 ]
  • [ 123-75-1 ]
  • [ 5724-81-2 ]
  • [ 13325-10-5 ]
Reference: [1] Patent: US2012/232292, 2012, A1, . Location in patent: Page/Page column 10; 12
[2] Patent: CN103502199, 2016, B, . Location in patent: Paragraph 0265; 0266
[3] Patent: JP2016/27052, 2016, A, . Location in patent: Paragraph 0088; 0095
[4] Patent: CN103502212, 2016, B, . Location in patent: Paragraph 0207-0208; 0212
  • 5
  • [ 56-12-2 ]
  • [ 13325-10-5 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 50, p. 6656 - 6659
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 22, p. 6346 - 6349
  • 6
  • [ 110-63-4 ]
  • [ 13325-10-5 ]
  • [ 110-60-1 ]
Reference: [1] Patent: US2012/232309, 2012, A1, . Location in patent: Page/Page column 14-15; 16
[2] Patent: US2012/232309, 2012, A1, . Location in patent: Page/Page column 14-15; 16
[3] Patent: US2012/232294, 2012, A1, . Location in patent: Page/Page column 13-14; 16
  • 7
  • [ 7606-22-6 ]
  • [ 13325-10-5 ]
Reference: [1] Synthesis, 1990, # 8, p. 735 - 738
[2] Journal of the Chemical Society, 1951, p. 2225,2226, 2229
[3] Chemical and Pharmaceutical Bulletin, 1961, vol. 9, p. 485 - 491
[4] Journal of Heterocyclic Chemistry, 1967, vol. 4, p. 298 - 300
  • 8
  • [ 110-63-4 ]
  • [ 123-75-1 ]
  • [ 93264-47-2 ]
  • [ 24715-90-0 ]
  • [ 41726-75-4 ]
  • [ 13325-10-5 ]
Reference: [1] Russian Journal of Organic Chemistry, 2016, vol. 52, # 12, p. 1756 - 1761[2] Zh. Org. Khim., 2016, vol. 52, # 12, p. 1765 - 1770,6
[3] Russian Journal of Organic Chemistry, 2016, vol. 52, # 12, p. 1756 - 1761[4] Zh. Org. Khim., 2016, vol. 52, # 12, p. 1765 - 1770,6
[5] Russian Journal of Organic Chemistry, 2016, vol. 52, # 12, p. 1756 - 1761[6] Zh. Org. Khim., 2016, vol. 52, # 12, p. 1765 - 1770,6
  • 9
  • [ 412274-79-4 ]
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YieldReaction ConditionsOperation in experiment
3.3 g With lithium aluminium tetrahydride In tetrahydrofuran for 1 h; Reflux The intermediate D (5.15 g, 50 mmol) from Example 2 was added to a 100 mL flask containing 50 mL of dry tetrahydrofuran, and lithium aluminum hydride (2.28 g, 60 mmol) was weighed and slowly added to the flask, followed by stirring. The reaction was refluxed for 1 h; after the reaction was completed, ethyl acetate was added to remove excess lithium aluminum hydride. The 10percent NaOH solution was added dropwise, and the addition was stopped when a pale yellow solid appeared. Finally, the solid was filtered off to obtain an organic layer. The solvent was removed, and a yellow oily liquid product (3.3 g) was obtained by distillation under reduced pressure to give the desired product
Reference: [1] Patent: CN104610075, 2017, B, . Location in patent: Paragraph 0051-0055
  • 10
  • [ 109-73-9 ]
  • [ 13325-10-5 ]
  • [ 114963-62-1 ]
Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 33, p. 8149 - 8150
  • 11
  • [ 1039627-16-1 ]
  • [ 13325-10-5 ]
  • [ 114963-62-1 ]
Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 27, p. 8669 - 8676
  • 12
  • [ 39711-80-3 ]
  • [ 13325-10-5 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1963, p. 1270 - 1272
  • 13
  • [ 110-63-4 ]
  • [ 109-99-9 ]
  • [ 123-75-1 ]
  • [ 13325-10-5 ]
Reference: [1] Journal of Organic Chemistry, 1994, vol. 59, # 14, p. 3998 - 4000
  • 14
  • [ 74-85-1 ]
  • [ 13325-10-5 ]
Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 1489,1492
  • 15
  • [ 4107-62-4 ]
  • [ 13325-10-5 ]
Reference: [1] Journal of the American Chemical Society, 1955, vol. 77, p. 1083,1085
  • 16
  • [ 3686-43-9 ]
  • [ 13325-10-5 ]
Reference: [1] Chemische Berichte, 1966, vol. 99, p. 561 - 565
  • 17
  • [ 628-22-8 ]
  • [ 13325-10-5 ]
Reference: [1] Dokaldy Akad.S.S.S.R., 1948, vol. 63, p. 282[2] Chem.Abstr., 1949, p. 2579
[3] Chem. Zentralbl., 1900, vol. 71, # II, p. 1008
[4] Chemische Berichte, 1900, vol. 33, p. 3170[5] Chem. Zentralbl., 1900, vol. 71, # II, p. 1008
  • 18
  • [ 928-51-8 ]
  • [ 13325-10-5 ]
Reference: [1] DRP/DRBP Org.Chem.,
[2] Journal of Organic Chemistry, 1965, vol. 30, p. 491 - 495
  • 19
  • [ 130340-72-6 ]
  • [ 13325-10-5 ]
  • [ 16135-31-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 7, p. 1824 - 1831
  • 20
  • [ 56-12-2 ]
  • [ 13325-10-5 ]
  • [ 109-73-9 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 7, p. 3097 - 3107
  • 21
  • [ 928-51-8 ]
  • [ 13325-10-5 ]
  • [ 79448-06-9 ]
Reference: [1] DRP/DRBP Org.Chem.,
  • 22
  • [ 1180496-62-1 ]
  • [ 13325-10-5 ]
  • [ 1180496-61-0 ]
Reference: [1] Journal of the American Chemical Society, 2009, vol. 131, # 32, p. 11274 - 11275
  • 23
  • [ 153363-51-0 ]
  • [ 13325-10-5 ]
Reference: [1] Gazzetta Chimica Italiana, 1993, vol. 123, # 10, p. 549 - 552
  • 24
  • [ 928-51-8 ]
  • [ 7664-41-7 ]
  • [ 13325-10-5 ]
  • [ 79448-06-9 ]
Reference: [1] DRP/DRBP Org.Chem.,
  • 25
  • [ 64-17-5 ]
  • [ 141-52-6 ]
  • [ 2453-49-8 ]
  • [ 13325-10-5 ]
Reference: [1] Doklady Akademii Nauk SSSR, 1948, vol. 63, p. 283[2] Chem.Abstr., 1949, p. 2579
  • 26
  • [ 67-56-1 ]
  • [ 13325-10-5 ]
  • [ 42042-68-2 ]
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 23, p. 7368 - 7377
[2] Catalysis Letters, 2016, vol. 146, # 7, p. 1182 - 1193
  • 27
  • [ 13325-10-5 ]
  • [ 109-94-4 ]
  • [ 42042-68-2 ]
YieldReaction ConditionsOperation in experiment
56%
Stage #1: for 18 h; Reflux; Inert atmosphere
Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran for 2 h; Reflux
Stage #3: With sodium hydroxide In tetrahydrofuran; water
To a stirred solution of 9 (4.31 g, 48.4 mmol) in EtOH (50 mL) was added ethylformate (5.86 mL, 75.5 mmol) and the mixture was stirred at reflux for 18 hrs under N2. The solution was evaporated under reduced pressure, and the crude product was used for the next step without further purification. The crude reaction mixture was dissolved in THF (25 mL) and added to a suspension of LiAlH4 (5.50 g, 145 mmol) in THF (50 mL) dropwise under a drying tube while stirring. The reaction mixture was brought to reflux and monitored by TLC (20percent EtOH/80percent CHC13) and JH NMR (CDC13). After 2 hours, the starting material was consumed, and 0 (4.16 mL) was added to the cooled reaction mixture, followed by 4 M NaOH (4.16 mL) and 0 (12.5 mL) while stirring vigorously. The precipitate was then removed by filtration, and the filtrate concentrated in vacuo. The residue was re-dissolved in CHCI3, dried over Na2S04, filtered and concentrated under reduced pressure to give 20 as a colorless oil (2.76 g, 56percent); JH NMR (CDC13) δ 3.74 (br, 2H), 3.57 (t, 2H), 2.62 (t, 2H), 2.43 (s, 3H), 1.50-1.75 (m, 4H).18
Reference: [1] Patent: WO2013/148230, 2013, A1, . Location in patent: Page/Page column 29; 30
  • 28
  • [ 67-56-1 ]
  • [ 13325-10-5 ]
  • [ 123-75-1 ]
  • [ 42042-68-2 ]
  • [ 13330-96-6 ]
Reference: [1] Angewandte Chemie - International Edition, 2002, vol. 41, # 18, p. 3476 - 3479
  • 29
  • [ 67-56-1 ]
  • [ 13325-10-5 ]
  • [ 123-75-1 ]
  • [ 42042-68-2 ]
  • [ 13330-96-6 ]
Reference: [1] Angewandte Chemie - International Edition, 2002, vol. 41, # 18, p. 3476 - 3479
  • 30
  • [ 50-00-0 ]
  • [ 13325-10-5 ]
  • [ 13330-96-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 22, p. 6346 - 6349
  • 31
  • [ 928-51-8 ]
  • [ 13325-10-5 ]
  • [ 79448-06-9 ]
Reference: [1] DRP/DRBP Org.Chem.,
  • 32
  • [ 928-51-8 ]
  • [ 7664-41-7 ]
  • [ 13325-10-5 ]
  • [ 79448-06-9 ]
Reference: [1] DRP/DRBP Org.Chem.,
  • 33
  • [ 13325-10-5 ]
  • [ 67-64-1 ]
  • [ 42042-71-7 ]
YieldReaction ConditionsOperation in experiment
100% With palladium 10% on activated carbon; hydrogen In ethanol 200 gm of 4-amino-1-butanol (II) was dissolved in a mixed solvent of 400 ml of acetone and 1000 ml of ethanol and, after adding 20 gm of 10percent Pd/C, hydrogenation was carried out under the pressure of 10 kg for 4-5 hours. The reaction solution was filtered to remove the catalyst and the filtrate obtained was concentrated to obtain desired compound in quantitative yield, as a colorless oily substance
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 18, p. 7128 - 7137
[2] Patent: WO2017/60827, 2017, A1, . Location in patent: Page/Page column 11
[3] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 21, p. 6692 - 6704
[4] Patent: EP1400518, 2004, A1, . Location in patent: Page 21
  • 34
  • [ 13325-10-5 ]
  • [ 24424-99-5 ]
  • [ 75178-87-9 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine In acetonitrile at 0℃; for 6.5 h; Inert atmosphere 4-amino-1-butanol (0.5 g, 5.61 mmol) was dissolved in acetonitrile (56 ml). The solution was cooled to 0°C and Et3N (1.56 ml, 11.22 mmol, 2 eq.) was added followed by Boc2O (1.346 g, 6.17 mmol). The reaction was followed by TLC and quenched with water (20 ml) after 6.5 h. The solution was extracted with EtOAc (3x30ml), brine was used to help phase separation. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel (CH2Cl2/MeOH, 95:5) to give the title compound as a colorless oil (1.06 g, quantitative yield)
100% With triethylamine In methanol at 0 - 20℃; To the solution of 4-aminobutanol (100 μL) in 2 mL triethylamine/methanol (Et3N/MeOH, v/v, 1:7) di-tert-butyl dicarbonate (278 μL) in 2.5 mL methanol was added dropwise at 0 °C. The solution was stirred at the same temperature overnight and allowed to warm to room temperature during 2 h and kept at ambient temperature for another 6 h. Upon completion of the reaction monitored by TLC visualized by iodine and ninhydin, excess Boc2O and solvent were removed under vacuum. The residue was partitioned between dichloromethane (CH2Cl2) and brine and extracted with CH2Cl2 (3 * 50 mL). The combined organic layers were washed by brine, then dried over MgSO4, filtered and concentrated in vacuo to provide tert-butyl N-(4-hydroxybutyl)carbamate 2 as colorless oil (152 mg, 100percent).
1H NMR (300 MHz, CDCl3) δ 5.02 (s, 1H), 3.63 (t, J = 6.1 Hz, 2H), 3.40 (s, 1H), 3.13 (d, J = 5.9 Hz, 2H), 1.56 (dd, J = 7.2, 4.1 Hz, 4H), 1.44 (s, 9H).
100% at 20℃; for 3 h; Butanolamine (5g, 56.09 mmol, 1.0 eq) is introduced in a round-bottomed flask with THF (20 mL) before dropwise addition of di-tert-butylcarbonate (12 mL, 56.09 mmol, 1.0 eq) in THF (10 mL). The reaction mixture is stirred at room temperature for 3 h. After concentration under vacuum, the desired product is obtained as an amorph solid that crystalize upon standing (10 g, quantitative yield).
100% at 20℃; for 3 h; To a solution of 4-amino-1 -butanol (2.0 g, 22.5 mmole) in THF at RT was added Boc anhydride (4.90 g, 22.5 mmole). After 3 h, the reaction solution was concentrated under vacuum and the residue purified on silica gel (hexanes/EtOAc, 1 :1 ) to give the title compound (quant.) as a white solid: LCMS (ES) m/z = 190 (M+H)+
96% With sodium hydroxide In 1,4-dioxane; water at 20℃; for 12 h; General procedure: To a solution of 2a (or 2b–e, 20 mmol) in a mixture of dioxane (15 mL) and H2O (7 mL), wasadded 5N NaOH (4.8 mL) and a solution of Boc2O (5.0 g, 23 mmol) in dioxane at 0 °C. After stirred atrt overnight, the reaction mixture was concentrated in vacuo. The residue was extracted from 10percentcitric acid with AcOEt, and dried over anhydrous Na2SO4. Evaporation of the solvents gave the pureproduct 3a–e. 3a was obtained as a colorless oil (2.67 g, 83percent).
90.2% at 0℃; for 4 h; General procedure: tert-butyl 3-hydroxypropylcarbamate 13a: Boc anhydride(319.2g, 1.46 mol) was added drop wise to 3-aminopropan-1-ol (100.0g, 1.33mol) in methanol ( 1000ml )at 0 °C. Reaction mixture was allowed to stir for 4hr. Reaction mixture was concentrated and diluted with water(1000ml) and ethylacetate (1000ml). Layers were separated.Organic layer was washed with water (250ml), dried oversodium sulfate and concentrated. 202.3g of clear liquid was obtained with 87percent yield. tert-butyl 4-hydroxybutylcarbamate 13b: Followingthe same procedure for 13a, 191.5g of clear liquid with90.2percent yield was obtained. 1H NMR (CDCl3) = 1.44 (s, 9H), 1.48(s, 1 H), 1.52-1.59 (m, 4 H), 3.12-3.16 (m, 2H,),3.66-3.68 (m, 2 H), 4.60-4.69 (br, s, 1 H), 13C NMR (CDCl3)= 26.61, 28.44, 29.74, 40.34, 62.31, 79.21, 156.22.
90.5% With triethylamine In dichloromethane at 20℃; for 12 h; 4-amino-1-butanol (40) (2.97 g) and triethylamine (5 mL) were added to dichloromethane (60ML), di-tert-butyl dicarbonate (6.61 g) was added under ice-cooling, and the mixture was stirred for 5 minutes. reactionThe solution was returned to room temperature and stirred for 12 hours.Under ice cooling, a 1 N hydrochloric acid aqueous solution was added to the reaction solution and further diluted with dichloromethane. After separating the organic layer, the obtained organic layer was washed with saturated brine and dried with anhydrous sodium sulfate. Filtration and concentration under reduced pressure gave the title compound (41) (5.71 g, yield 90.5percent) as a pale yellow oil.
89% at 20℃; for 1.5 h; N-tert-Butoxycarbonyl-4-amino-1-butanol 4-Amino-1-butanol (1.0 g, 11.22 mmol) was dissolved in methanol (10 ml). To this solution, di-tert-butyl carbonate (2.53 g, 11.58 mmol) was added, and the mixture was stirred at room temperature for 1.5 hours. After the reaction was confirmed by TLC to be complete, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:acetone=9:1) to obtain N-tert-butoxycarbonyl-4-amino-1-butanol (1.88 g, yield: 89percent).
88% With triethylamine In dichloromethane at 20℃; for 2 h; To a mixture of 4-aminobutan-l-ol (4.0 g, 45 mmol) and TEA (7.5 mL, 54 mmol) in DCM (200 ml) was added (Boc)20 (10.2 g, 47.2 mmol). The reaction mixture was stirred for 2 h at room temperature and then washed with water (2x150 mL) and the solution of citric acid (100 mL). The organic layer was dried over anhydrous Na2S04 and concentrated to give the product as yellow oil 7.5 g. (yield 88percent).
82% With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 1.5 h; 4-Aminobutan-1-ol (1.0 g, 11.2 mmol) was suspended in a mixture of dioxane (20 ml), H2O (10 ml) and 1 M NaOH (10 ml) and cooled to 0 °C (ice-water bath) with stirring. Boc2O (2.69 g, 12.34 mmol) was added and stirring was continued at ambient temperature. After 5.5 h additional Boc2O (1.08 g, 4.95 mmol) was added and stirring was continued overnight. Next day additional Boc2O (1.35 g, 6.19 mmol) was added to the suspension. After 1.5 h sulfate buffer (40 ml) was added and the reaction mixture was transferred to a separating funnel and extracted with EtOAc (3 × 30 ml). The combined organic layers were washed with NaHCO3(90 ml) and brine (90 ml), dried (Na2SO4), filtered and concentrated in vacuo. Purification by flash column chromatography (60 percent EtOAc in n-heptane, v/v) gave carbamate 4 (1.62 g, 82percent) as a colourless oil.
54% With N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; for 24 h; Inert atmosphere A mixture of 4-aminobutan-1-ol (10.0 g, 112.1 mmol, 10.4 mL, 1.0 eq), tert- butoxycarbonyl tert-butyl carbonate (25.7 g, 117.8 mmol, 27.1 mL, 1.05 eq) and DIEA (21.7 g, 168.2 mmol, 29.3 mL, 1.5 eq) in DCE (400 mL) was stirred at 20 °C for 24 h, diluted with water (400 mL) and extracted with DCM (100 mL*3). The combined organic layers were washed with brine (100 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2) to give compound 07-4-1 (12.0 g, 60.2 mmol, 54percent yield).1H NMR (CDCl3, 400 MHz): δ 3.67 (d, J=4.85 Hz, 2 H), 3.16 (d, J=5.29 Hz, 2 H), 1.54 - 1.62 (m, 4 H), 1.44 (s, 9 H).
7.54 g at 20℃; for 24 h; Cooling with ice Reference Example 35 tert-Butyl 4-hydroxybutylcarbamate (0486) (0487) To a mixture of 4-aminobutanol (3.57 g) and ethyl acetate (9 mL) was dropwise added a mixture of di-tert-butyl dicarbonate (8.73 g) and ethyl acetate (1 mL) under ice-cooling. After stirring at room temperature for 24 hrs., the mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (200 mL), and the mixture was washed with water (50 mL), 1N hydrochloric acid (40 mL), water (30 mL) and saturated brine (30 mL) and dried over anhydrous magnesium sulfate. Concentration under reduced pressure gave the title compound (7.54 g) as a colorless oil. (0488) 1H-NMR(CDCl3): 1.44 (9H, s), 1.47-1.61 (4H, m), 3.07-3.22 (2H, m), 3.61-3.76 (2H, m), 4.62 (1H, bs).

Reference: [1] Organic Letters, 2009, vol. 11, # 9, p. 2019 - 2022
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 6, p. 2536 - 2543
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 1151 - 1155
[4] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 2, p. 191 - 200
[5] Inorganica Chimica Acta, 2016, vol. 452, p. 152 - 158
[6] Patent: WO2006/113837, 2006, A2, . Location in patent: Page/Page column 78
[7] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 8, p. 803 - 808
[8] Chemistry - A European Journal, 2016, vol. 22, # 9, p. 3009 - 3018
[9] Synthesis, 1990, p. 366 - 368
[10] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 23, p. 7050 - 7053
[11] Synthesis, 2011, # 24, p. 3991 - 3996
[12] Tetrahedron Letters, 2008, vol. 49, # 29-30, p. 4491 - 4493
[13] Journal of Medicinal Chemistry, 2009, vol. 52, # 22, p. 7029 - 7043
[14] Tetrahedron Letters, 1998, vol. 39, # 32, p. 5697 - 5700
[15] Bioorganic Chemistry, 2002, vol. 30, # 2, p. 81 - 94
[16] Angewandte Chemie - International Edition, 2012, vol. 51, # 32, p. 8110 - 8113
[17] Molecules, 2013, vol. 18, # 11, p. 13957 - 13978
[18] Journal of Medicinal Chemistry, 2014, vol. 57, # 11, p. 4924 - 4939
[19] Journal of Medicinal Chemistry, 2015, vol. 58, # 13, p. 5287 - 5307
[20] Journal of Medicinal Chemistry, 2006, vol. 49, # 14, p. 4183 - 4195
[21] Farmaco, 1991, vol. 46, # 12, p. 1517 - 1529
[22] Letters in Organic Chemistry, 2013, vol. 10, # 7, p. 518 - 522
[23] Patent: JP2017/71567, 2017, A, . Location in patent: Paragraph 0208-0210
[24] Patent: US2015/353489, 2015, A1, . Location in patent: Paragraph 0070; 0181; 0182
[25] Patent: WO2012/33858, 2012, A2, . Location in patent: Page/Page column 85
[26] Journal of Organic Chemistry, 2010, vol. 75, # 2, p. 518 - 521
[27] Helvetica Chimica Acta, 1996, vol. 79, # 8, p. 2137 - 2151
[28] Journal of Medicinal Chemistry, 2015, vol. 58, # 17, p. 6819 - 6843
[29] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 644 - 647
[30] Journal of Labelled Compounds and Radiopharmaceuticals, 2007, vol. 50, # 7, p. 666 - 670
[31] Chemical Communications, 2006, # 20, p. 2156 - 2158
[32] Journal of Medicinal Chemistry, 2014, vol. 57, # 22, p. 9673 - 9686
[33] Patent: WO2017/96045, 2017, A1, . Location in patent: Paragraph 00883
[34] Tetrahedron Letters, 1997, vol. 38, # 33, p. 5741 - 5744
[35] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 21, p. 4828 - 4832
[36] Journal of Medicinal Chemistry, 2004, vol. 47, # 24, p. 6055 - 6069
[37] Journal of Medicinal Chemistry, 2005, vol. 48, # 11, p. 3832 - 3839
[38] Journal of the Chemical Society, Perkin Transactions 2, 2002, # 5, p. 923 - 927
[39] Tetrahedron Letters, 2004, vol. 45, # 38, p. 7081 - 7085
[40] Patent: US5965591, 1999, A,
[41] Patent: WO2003/105845, 2003, A1, . Location in patent: Page 88-89
[42] Patent: EP1602362, 2005, A1, . Location in patent: Page/Page column 50
[43] Patent: EP1607088, 2005, A1, . Location in patent: Page/Page column 53
[44] Biomacromolecules, 2012, vol. 13, # 5, p. 1632 - 1641
[45] Angewandte Chemie - International Edition, 2014, vol. 53, # 3, p. 883 - 887[46] Angew. Chem., 2013, vol. 53, # 3, p. 902 - 906
[47] Tetrahedron Letters, 2015, vol. 56, # 51, p. 7108 - 7111
[48] Patent: US2016/128945, 2016, A1, . Location in patent: Paragraph 0486; 0487; 0488
[49] Biomacromolecules, 2016, vol. 17, # 11, p. 3632 - 3639
[50] Journal of Medicinal Chemistry, 2017, vol. 60, # 16, p. 7067 - 7083
[51] Tetrahedron, 2016, vol. 72, # 41, p. 6492 - 6498
[52] Journal of Medicinal Chemistry, 2018, vol. 61, # 11, p. 4961 - 4977
[53] ChemMedChem, 2018, vol. 13, # 18, p. 1957 - 1971
  • 35
  • [ 13325-10-5 ]
  • [ 34619-03-9 ]
  • [ 75178-87-9 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 20, p. 6278 - 6287
  • 36
  • [ 13325-10-5 ]
  • [ 33545-98-1 ]
Reference: [1] Patent: US2012/108515, 2012, A1,
  • 37
  • [ 13325-10-5 ]
  • [ 24566-81-2 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2000, vol. 37, # 6, p. 1431 - 1438
[2] British Journal of Pharmacology, 1996, vol. 117, # 4, p. 619 - 632
[3] Tetrahedron, 2013, vol. 69, # 36, p. 7699 - 7705
  • 38
  • [ 13325-10-5 ]
  • [ 24424-99-5 ]
  • [ 99207-32-6 ]
Reference: [1] Patent: EP1184373, 2002, A1, . Location in patent: Example 89
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