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Chemical Structure| 107017-73-2
Chemical Structure| 107017-73-2
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Product Details of [ 107017-73-2 ]

CAS No. :107017-73-2 MDL No. :MFCD09749954
Formula : C9H17NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :HFMAZNJKNNRONT-UHFFFAOYSA-N
M.W : 187.24 Pubchem ID :11286907
Synonyms :

Calculated chemistry of [ 107017-73-2 ]      Expand+

Physicochemical Properties

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 : 48.98
TPSA : 58.56 Ų

Pharmacokinetics

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) : -7.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.93
Log Po/w (XLOGP3) : 0.62
Log Po/w (WLOGP) : 0.97
Log Po/w (MLOGP) : 0.56
Log Po/w (SILICOS-IT) : 0.78
Consensus Log Po/w : 0.97

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.06
Solubility : 16.3 mg/ml ; 0.0868 mol/l
Class : Very soluble
Log S (Ali) : -1.42
Solubility : 7.05 mg/ml ; 0.0376 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.48
Solubility : 6.19 mg/ml ; 0.033 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.15

Safety of [ 107017-73-2 ]

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 [ 107017-73-2 ]

* 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 [ 107017-73-2 ]
  • Downstream synthetic route of [ 107017-73-2 ]

[ 107017-73-2 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 107017-73-2 ]
  • [ 88950-64-5 ]
Reference: [1] European Journal of Organic Chemistry, 2000, # 18, p. 3235 - 3245
[2] Synthesis, 2010, # 20, p. 3410 - 3414
[3] Journal of Organic Chemistry, 2002, vol. 67, # 11, p. 3965 - 3968
  • 2
  • [ 107259-05-2 ]
  • [ 107017-73-2 ]
YieldReaction ConditionsOperation in experiment
79% With lithium borohydride In tetrahydrofuran at 23℃; Ethyl 1-((tert-butoxycarbonyl)amino)cyclopropanecarboxylate (4.31 g, 18.80 mmol) was dissolved indry THE (20 mL), 2 M L1BH4 in THE (10.34 mL, 20.68 mmol) was added dropwise and the reactionmixture was stirred at RT overnight. More 2 M LiBH4 in THF (5 mL, 10 mmol) was added and stirring at RTwas continued for6 h. Na2SO4 (15 g)was added followed by H20 (10 mL). The suspension was stirred at RT over the weekend. The suspension was filtered over a pad of Na2SO4 and the residue washed with DCM. The combined filtrate was evaporated under reduced pressure. The product waspurified by CC (silica, heptane/EtOAc, 1:1), to furnish 2.78 g (79percent) of the desired product.
61% With lithium borohydride In tetrahydrofuran at 20℃; for 17.6667 h; [0505] To a suspension of 1-aminocyclopropanecarboxylic acid (998 mg, 9.87 mmol) in EtOH (25 mL), cooled to 0° C., was added SOCl2 (2.0 mL, 27 mmol) dropwise over 10 minutes. The resulting solution was heated at reflux under nitrogen for 2 hours, then was evaporated under reduced pressure, giving the ester as a light brown oil. [0506] This material was dissolved into EtOAc (25 mL) and a solution of KHCO3 (1.51 g, 15.1 mmol) in H2O (9 mL) was added dropwise. The resulting solution was cooled to 0° C. and a solution of Boc2O (2.97 g, 13.6 mmol) in EtOAc (10 mL) was added. The reaction was stirred at room temperature for 16 hours, the layers were separated and the aqueous solution was extracted with EtOAc (25 mL). The combined organic solution was dried (MgSO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica (EtOAc/hexane, 1:3) gave the protected amine as light brown solid (1.27 g, 5.54 mmol, 56percent). 1H NMR (CDCl3) δ 1.08-1.18 (m, 2H), 1.23 (t, 3H, J=7.2 Hz), 1.44 (s, 9H), 1.46-1.53 (m, 2H), 4.14 (q, 2H, J=7.2 Hz), 5.13 (br. s, 1H). [0507] Preparation of (1-hydroxymethyl-cyclopropyl)-carbamic Acid Tert-Butyl Ester: [0508] To a solution of the ester (1.18 g, 5.15 mL) in THF (10 mL) under nitrogen was added a solution of LiBH4 (200 mg, 9.2 mmol) in THF (10 mL) dropwise over 10 minutes. The reaction was stirred at room temperature for 17.5 hours, then was cooled to 0° C. A solution of 50percent HOAc was added dropwise until the evolution of gas had ceased (approx. 8 mL). The resulting white suspension was diluted with H2O (15 mL) and was extracted with Et2O (30 mL). The organic solution was washed with 15percent aqueous NaHCO3 (15 mL) and brine (15 mL), then dried (Na2SO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica (EtOAc/hexane, 1:1) gave the alcohol as a white solid (592 mg, 3.16 mmol, 61percent).2 1H NMR (CDCl3) δ 0.81 (s, 4H), 1.43 (s, 9H), 3.52 (br. s, 1H), 3.58 (s, 2H), 5.12 (br. s, 1H). [0509] Preparation of (1-formyl-cyclopropyl)-carbamic Acid Tert-Butyl Ester: [0510] To a solution of the alcohol (389 mg, 2.08 mmol) in CH2Cl2 (11 mL), cooled to 0° C., was added crushed, dried 3 molecular sieves (1.05 g), NMO (382 mg, 3.26 mmol) and TPAP (76 mg, 0.22 mmol). The black mixture was stirred at 0° C. for 30 minutes and at room temperature for a further 30 minutes. The mixture was diluted with EtOAc (20 mL) and flushed through a short silica column, rinsing with EtOAc. The product containing material was concentrated under reduced pressure giving the aldehyde as a white solid (345 mg, 1.86 mmol, 90percent). 1H NMR (CDCl3) δ 1.27-1.37 (m, 2H), 1.40-1.52 (m, 2H), 1.46 (s, 9H), 5.22 (br. s, 1H), 9.16 (s, 1H). [0511] Preparation of (E)-3-(i-tert-butoxycarbonylamino-cyclopropyl)-acrylic Acid Ethyl Ester: [0512] Triethyl phosphonoacetate (0.62 mL, 3.13 mmol) was added dropwise to a suspension of 60percent NaH in mineral oil (120 mg, 3.00 mmol) in THF (5 mL). The resulting solution was stirred at room temperature for 10 minutes, then cooled to 0° C. for the dropwise addition of a solution of the aldehyde (463 mg, 2.50 mmol) in THF (5 mL). The reaction was stirred at 0° C. for 15 minutes, then heated to reflux for 1 hour. Once cooled to room temperature, saturated aqueous NH4Cl (10 mL) was added, the layers were separated and the aqueous solution was extracted with CH2Cl2 (10 mL.x.2). The organic solution was dried (MgSO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica (EtOAc/hexane, 1:1) gave the unsaturated ester as a pale yellow solid (539 mg, 2.11 mmol, 84percent). 1H NMR (CDCl3) δ 1.11-1.18 (m, 2H), 1.24-1.29 (m, 5H), 1.44 (s, 9H), 4.17 (q, 2H, J=7.1 Hz), 5.02 (br. s, 1H), 5.84 (d, 1H, J=15.3 Hz), 6.47 (d, 1H, J=15.6 Hz). [0513] Preparation of 3-(1-tert-butoxycarbonylamino-cyclopropyl)-propionic Acid Ethyl Ester: [0514] A solution of the unsaturated ester (495 mg, 1.94 mmol) in EtOAc (10 mL) was hydrogenated (H2 balloon) over 10percent Pd/C (25 mg, 0.023 mmol) at room temperature for 3 hours. The mixture was suction filtered through Celite, washing with EtOAc and evaporation of the filtrate under reduced pressure gave the saturated ester as a colourless oil (500 mg, 1.94 mmol, 100percent). 1H NMR (CDCl3) δ 0.61-0.65 (m, 1H), 0.73-0.78 (m, 1H), 0.91 (t, 2H, J=7.4 Hz), 1.25 (td, 3H, J=7.1, 1.4 Hz), 1.43 (s, 9H), 1.78-1.90 (m, 2H), 2.36 (t, 1H, J=7.7 Hz), 2.44 (t, 1H, J=7.5 Hz), 4.12 (q, 2H, J=7.1 Hz). [0515] Preparation of [1-(3-hydroxy-propyl)-cyclopropyl]-carbamic Acid Tert-Butyl Ester: [0516] LiBH4 (70 mg, 3.2 mmol) was added to a solution of the ester (500 mg, 1.94 mmol) in THF (8 mL). The reaction was stirred at room temperature under nitrogen for 18 hours, then was quenched by the dropwise addition of 50percent aqueous HOAc until the evolution of gas had ceased (approx. 2 mL). The suspension was diluted with H2O (10 mL) and extracted with Et2O (15 mL). The organic solution was washed with saturated aqueous NaHCO3 (10 mL) and brine (10 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica (hexane/EtOAc, 2:1; increased to 1:1) gave the alcohol as a colourless oil (164 mg, 0.77 mmol, 40percent). 1H NMR (CDCl3) δ 0.55-0.62 (m, 2H), 0.69-0.75 (m, 2H), 1.40 (s, 9H), 1.52-1.72 (m, 4H), 2.10 (br. s, 1H), 3.64 (t, 2H, J=6.3 Hz), 4.96 (br. s, 1H). [0517] Preparation of {1-[3-(5,6,7,8-tetrahydro-quinolin-8-ylamino)-propyl]-cyclopropyl}-carbamic Acid Tert-Butyl Ester: [0518] To a solution of the alcohol (160 mg, 0.74 mmol) in CH2Cl2 (4 mL), cooled to 0° C., was added crushed, dried 3A molecular sieves (374 mg), NMO (125 mg, 1.07 mmol) and TPAP (26 mg, 0.07 mmol). The reaction was stirred at 0° C. for 25 minutes, then at room temperature for a further 15 minutes. The reaction was diluted with EtOAc (8 mL) and the mixture was flushed through a short silica column, eluting with EtOAc. Removal of the solvent under reduced pressure gave the aldehyde as a pale yellow oil (123 mg, 78percent). [0519] A solution of this material (120 mg, 0.56 mmol) and 8-amino-5,6,7,8-tetrahydroquinoline (90 mg, 0.61 mmol) in MeOH (1.5 mL) was stirred at room temperature under nitrogen for 17 hours. NaBH4 (35 mg, 0.93 mmol) was added and the reaction was stirred for a further 15 minutes. The solvent was evaporated under reduced pressure, the residue was taken up into CH2Cl2 (20 mL) and was washed with saturated aqueous NaHCO3 (5 mL) and brine (5 mL). The organic solution was dried (MgSO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica (CH2Cl2/MeOH/NH4OH, 19:1:0.1) gave the secondary amine as an orange oil (51 mg, 0.15 mmol, 26percent). 1H NMR (CDCl3) δ 0.57-0.63 (m, 2H), 0.69-0.76 (m, 2H), 1.42 (s, 9H), 1.56-1.80 (m, 5H), 1.80-2.06 (m, 3H), 2.09-2.20 (m, 1H), 2.68-2.87 (m, 4H), 3.77 (t, 1H, J=6.3 Hz), 5.16 (br. s, 1H), 7.06 (dd, 1H, J=7.7, 4.7 Hz), 7.37 (d, 1H, J=7.5 Hz), 8.38 (d, 1H, J=4.2 Hz). [0520] Preparation of 2-[[3-(1-tert-butoxycarbonylamino-cyclopropyl)-propyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzimidazole-1-carboxylic Acid Tert-Butyl Ester: [0521] A solution of the secondary amine (51 mg, 0.147 mmol), tert-butyl 2-chloro-methylbenzimidazole-1-carboxylate (47 mg, 0.18 mmol), DIPEA (0.04 mL, 0.2 mmol) and KI (5 mg, 0.03 mmol) in CH3CN (0.8 mL) was stirred at 60° C. under nitrogen for 18 hours. Once cooled to room temperature, saturated aqueous NaHCO3 (5 mL) was added and the mixture was extracted with CH2Cl2 (10 mL.x.3). The combined organic solution was dried (MgSO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica (CH2Cl2/MeOH/NH4OH, 19:1:0.1) gave the tertiary amine as a pale orange foam (60 mg, 0.104 mmol, 71percent). 1H NMR (CDCl3) δ 0.30-0.46 (m, 2H), 0.48-0.63 (m, 2H), 1.29-1.50 (m, 11H), 1.60-1.76 (m, 12H), 1.79-1.90 (m, 1H), 1.95-2.05 (m, 1H), 2.08-2.19 (m, 1H), 2.59-2.70 (m, 2H), 2.72-2.87 (m, 2H), 4.26 (dd, 1H, J=9.5, 6.5 Hz), 4.50 (d, 1H, J=15.6 Hz), 4.63 (d, 1H, J=15.0 Hz), 5.10 (br. s, 1H), 6.98 (dd, 1H, J=7.7, 4.7 Hz), 7.26-7.32 (m, 3H), 7.72 (dd, 1H, J=6.2, 3.2 Hz), 7.83 (dd, 1H, J=6.0, 3.0 Hz), 8.37 (d, 1H, J=3.0 Hz). [0522] Preparation of COMPOUND 49: [0523] To a solution of the tertiary amine (57.6 mg, 0.100 mmol) in glacial HOAc (1.0 mL) was added a saturated solution of HBr in HOAc (0.5 mL). The reaction was stirred at room temperature for one hour and Et2O (5 mL) was added. The resulting sticky solid was washed with Et2O (1 mL.x.2), then crushed with a spatula while under Et2O (2 mL). The resulting precipitate was washed with Et2O (1 mL.x.2), then dried under reduced pressure affording COMPOUND 49 as an orange powder (65.7 mg, 0.091 mmol, 91percent). 1H NMR (D2O) δ 0.63-0.68 (m, 2H), 0.81-0.86 (m, 2H), 1.46-1.67 (m, 4H), 1.76-1.90 (m, 1H), 1.93-2.06 (m, 1H), 2.12-2.22 (m, 1H), 2.31-2.41 (m, 1H), 2.48-2.58 (m, 1H), 2.77-2.87 (m, 1H), 2.96-3.02 (m, 2H), 4.39 (d, 1H, J=16.8 Hz), 4.47-4.56 (m, 2H), 7.59 (dd, 2H, J=6.2, 3.2 Hz), 7.79 (dd, 2H, J=6.2, 3.2 Hz), 7.85 (dd, 1H, J=7.8, 6.0 Hz), 8.33 (d, 1H, J=7.8 Hz), 8.62 (d, 1H, J=5.4 Hz). 13C NMR (D2O) δ 9.6, 20.4, 24.3, 27.6, 31.8, 34.3, 48.0, 51.8, 60.5, 114.3, 125.9, 126.9, 131.0, 139.3, 140.6, 148.1, 151.2, 151.7. ES-MS m/z 376 (M+H). Anal. Calcd. for C23H29N5.3.1HBr.1.5C2H4O2.0.2H2O: C, 43.37; H, 5.39; N, 9.73; Br, 34.40. Found: C, 43.26; H, 5.67; N, 9.64; Br, 34.68.
Reference: [1] Journal of Medicinal Chemistry, 1988, vol. 31, # 9, p. 1694 - 1697
[2] Patent: WO2015/90603, 2015, A1, . Location in patent: Page/Page column 59; 60
[3] Journal of Medicinal Chemistry, 1988, vol. 31, # 10, p. 2004 - 2008
[4] Patent: US2003/220341, 2003, A1, . Location in patent: Page/Page column 49-50
[5] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 7, p. 2151 - 2155
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  • [ 66494-26-6 ]
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 2188 - 2193
[2] Patent: US2010/317698, 2010, A1, . Location in patent: Page/Page column 8
[3] Patent: US2015/152068, 2015, A1, . Location in patent: Paragraph 0237; 0238
[4] Patent: WO2015/79417, 2015, A1, . Location in patent: Paragraph 50
[5] Patent: WO2017/37221, 2017, A1, . Location in patent: Page/Page column 90
[6] Patent: WO2016/164580, 2016, A1, . Location in patent: Page/Page column 255;
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  • [ 88950-64-5 ]
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YieldReaction ConditionsOperation in experiment
1.04 g
Stage #1: With 4-methyl-morpholine; isobutyl chloroformate In 1,2-dimethoxyethane at -70 - -5℃;
Stage #2: With sodium tetrahydroborate In 1,2-dimethoxyethane at -15 - 20℃; for 0.5 h;
8.1
tert-butyl (1-hydroxymethylcyclopropyl)-carbamidate
1 g 1-(BOC-amino)-cyclopropanecarboxylic acid is dissolved in 20 ml dimethoxyethane and cooled to -70° C.
Then 0.65 ml N-methylmorpholine are added and 0.71 ml isobutylchloroformate in 5 ml dimethoxyethan are added dropwise.
The reaction mixture is heated to -5° C.
The precipitate is suction filtered.
The eluate is cooled to -15° C. and 0.303 g sodium borohydride are slowly added.
The reaction mixture is then stirred for 30 minutes at ambient temperature, mixed with water and the product is extracted with dichloromethane.
The organic phase is dried and evaporated to dryness.
1.04 g product are obtained as a solid. 1H NMR (400 MHz, DMSO): 1.36 (9H, s); 0.61 (2H, t); 0.52 (2H, t).
1.04 g With 4-methyl-morpholine; sodium tetrahydroborate; isobutyl chloroformate In 1,2-dimethoxyethane at -70 - 20℃; 2.1
tert-butyl(1-hydroxymethylcyclopropyl)-carbamidate
1 g 1-(BOC-amino)-cyclopropanecarboxylic acid is dissolved in 20 ml dimethoxyethane and cooled to -70° C.
Then 0.65 ml N-methylmorpholine are added and 0.71 ml isobutylchloroformate in 5 ml dimethoxyethane are added dropwise.
The reaction mixture is heated to -5° C.
The precipitate is suction filtered.
The eluate is cooled to -15° C. and 0.303 g sodium borohydride are slowly added.
The reaction mixture is then stirred for 30 minutes at ambient temperature, mixed with water and the product is extracted with dichloromethane.
The organic phase is dried and evaporated to dryness.
1.04 g product are obtained as a solid. 1H NMR (400 MHz, DMSO): 1.36 (9H, s); 0.61 (2H, t); 0.52 (2H, t).
4.24 g
Stage #1: With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -20℃; for 0.333333 h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 0.666667 h;
A solution of 1-(N-tert-butoxycarbonylamino)cyclopropanecarboxylic acid (5 g) in tetrahydrofuran was cooled to -20° C. Isobutyl chloroformate (3.24 ml) and N-methylmorpholine (2.74 ml) were added thereto, and the mixture was stirred at the same temperature as above for 20 minutes.
Then, sodium borohydride (1.12 g) and water (1 ml) were added thereto, and the mixture was further stirred at room temperature for 40 minutes.
Water was added to the reaction solution, followed by extraction with ethyl acetate.
The extract was washed with water and saturated saline in this order and then dried over anhydrous sodium sulfate.
The solvent was distilled off under reduced pressure.
The obtained residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain the title compound (4.24 g).
1H-NMR (CDCl3) δ: 0.81-0.85 (4H, m), 1.44 (9H, s), 3.43 (1H, br s), 3.59 (2H, d, J=4.8 Hz), 5.07 (1H, br s).
Reference: [1] Patent: US2010/305102, 2010, A1, . Location in patent: Page/Page column 16
[2] Patent: US2011/21501, 2011, A1, . Location in patent: Page/Page column 58-59
[3] Patent: US2011/28441, 2011, A1, . Location in patent: Page/Page column 14
[4] Patent: US2011/46096, 2011, A1, . Location in patent: Page/Page column 23
[5] Patent: US2013/237527, 2013, A1, . Location in patent: Paragraph 0223; 0224
[6] Patent: US2013/225609, 2013, A1, . Location in patent: Paragraph 0274; 0275
[7] Patent: US2016/46639, 2016, A1, . Location in patent: Paragraph 0275; 0276
[8] Patent: WO2016/206101, 2016, A1, . Location in patent: Page/Page column 186
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YieldReaction ConditionsOperation in experiment
51.2% With dmap; triethylamine In dichloromethane at 20℃; for 3 h; Inert atmosphere Di-t-butyldicarbonate (6.23 g, 28.57 mmol) was added to 1 -amino-cyclopropanemethanol hydrochloride (2.943 g, 23.81 mmol), triethylamine (8.31 mL, 59.52 mmol) and 4- dimethylaminopyridine (0.291 g, 2.38 mmol) in DCM (90 mL) under nitrogen. The resulting solution was stirred at 20 °C for 3 hours. It was washed with saturated aqueous sodium bicarbonate (20 mL), dried (sodium sulfate) and concentrated in vacuo to a colourless gum (3.277 g). It was taken up in DCM, concentrated in vacuo and adsorbed onto silica. The crude product was purified by flash silica chromatography, elution gradient0 to 100percent EtOAc in heptane. Pure fractions were evaporated to dryness to afford tert-butyl (1-(hydroxymethyl)cyclopropyl)carbamate (2.283 g, 51.2 percent) as a white solid. ‘H NMR (400 MHz, DMSO, 30°C) 0.48 - 0.55 (2H, m), 0.58 - 0.64 (2H, m), 1.36 (9H, s), 3.36 (2H, d), 4.51 (1H, t), 6.98 (1H, s).
Reference: [1] Patent: WO2016/162325, 2016, A1, . Location in patent: Page/Page column 124; 125
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Reference: [1] European Journal of Organic Chemistry, 2000, # 18, p. 3235 - 3245
[2] Journal of Organic Chemistry, 2002, vol. 67, # 11, p. 3965 - 3968
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Reference: [1] Synthesis, 2010, # 20, p. 3410 - 3414
[2] Organic and Biomolecular Chemistry, 2005, vol. 3, # 19, p. 3482 - 3487
[3] Patent: WO2013/52394, 2013, A1, . Location in patent: Paragraph 00258
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  • [ 88950-64-5 ]
  • [ 543-27-1 ]
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YieldReaction ConditionsOperation in experiment
4.24 g
Stage #1: With 4-methyl-morpholine In tetrahydrofuran at -20℃; for 0.333333 h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 0.666667 h;
Stage #3: With water In tetrahydrofuran
Step 1
tert-Butyl N-[1-(hydroxymethyl)cyclopropyl]carbamate
A solution of 1-(N-tert-butoxycarbonylamino)cyclopropanecarboxylic acid (5 g) in tetrahydrofuran was cooled to -20° C. Isobutyl chloroformate (3.24 ml) and N-methylmorpholine (2.74 ml) were added thereto, and the mixture was stirred at the same temperature as above for 20 minutes.
Then, sodium borohydride (1.12 g) and water (1 ml) were added thereto, and the mixture was further stirred at room temperature for 40 minutes.
Water was added to the reaction solution, followed by extraction with ethyl acetate.
The extract was washed with water and saturated saline in this order and then dried over anhydrous sodium sulfate.
The solvent was distilled off under reduced pressure.
The obtained residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain the title compound (4.24 g).
1H-NMR (CDCl3) δ: 0.81-0.85 (4H, m), 1.44 (9H, s), 3.43 (1H, br s), 3.59 (2H, d, J=4.8 Hz), 5.07 (1H, br s).
Reference: [1] Patent: US2012/28932, 2012, A1,
[2] Patent: US2012/35143, 2012, A1,
[3] Patent: US2015/51190, 2015, A1, . Location in patent: Paragraph 0218-0220
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Reference: [1] Patent: WO2009/70485, 2009, A1, . Location in patent: Page/Page column 124
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Reference: [1] Patent: WO2011/119759, 2011, A1, . Location in patent: Page/Page column 132
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  • [ 24424-99-5 ]
  • [ 107017-73-2 ]
Reference: [1] Journal of Organic Chemistry, 2002, vol. 67, # 11, p. 3965 - 3968
[2] European Journal of Organic Chemistry, 2000, # 18, p. 3235 - 3245
[3] Patent: WO2011/119759, 2011, A1,
[4] Patent: WO2015/90603, 2015, A1,
[5] Patent: WO2013/52394, 2013, A1,
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Reference: [1] Patent: US4603011, 1986, A,
[2] Patent: US4622418, 1986, A,
  • 13
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Reference: [1] Synthesis, 2010, # 20, p. 3410 - 3414
  • 14
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  • [ 115652-52-3 ]
YieldReaction ConditionsOperation in experiment
0.5 g With hydrogenchloride In 1,4-dioxane at 20℃; for 15 h; 8.2
1-aminocyclopropanemethanol
1.04 g tert-butyl (1-hydroxymethylcyclopropyl)-carbamidate are placed in 5 ml dioxane. 2.5 ml of HCl in dioxane (4 mol/l) are added dropwise.
The reaction mixture is stirred for 15 h at ambient temperature.
The solvent is evaporated down by half and the precipitated solid is suction filtered.
0.5 g product are obtained as the hydrochloride. 1H NMR (400 MHz, DMSO): 5.27 (1H, t); 0.91 (2H, t); 0.71 (2H, t).
Reference: [1] Journal of Medicinal Chemistry, 1988, vol. 31, # 10, p. 2004 - 2008
[2] European Journal of Organic Chemistry, 2005, # 11, p. 2250 - 2258
[3] Patent: US2010/305102, 2010, A1, . Location in patent: Page/Page column 16
[4] Patent: US2011/21501, 2011, A1, . Location in patent: Page/Page column 59
[5] Patent: US2011/28441, 2011, A1, . Location in patent: Page/Page column 14
[6] Patent: US2011/46096, 2011, A1, . Location in patent: Page/Page column 23
[7] Patent: US2013/237527, 2013, A1, . Location in patent: Paragraph 0225; 0226
  • 15
  • [ 107017-73-2 ]
  • [ 1027338-34-6 ]
Reference: [1] European Journal of Organic Chemistry, 2005, # 3, p. 600 - 609
[2] Patent: WO2013/52394, 2013, A1,
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