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[ CAS No. 2508-29-4 ]

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Chemical Structure| 2508-29-4
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CAS No. :2508-29-4 MDL No. :MFCD00008237
Formula : C5H13NO Boiling Point : 222.4°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :103.16 g/mol Pubchem ID :75634
Synonyms :

Safety of [ 2508-29-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P280-P305+P351+P338-P310 UN#:2735
Hazard Statements:H302-H314 Packing Group:
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Application In Synthesis of [ 2508-29-4 ]

  • Upstream synthesis route of [ 2508-29-4 ]
  • Downstream synthetic route of [ 2508-29-4 ]

[ 2508-29-4 ] Synthesis Path-Upstream   1~12

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  • [ 85-44-9 ]
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Reference: [1] Patent: US5654431, 1997, A,
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  • [ 7789-60-8 ]
  • [ 63273-48-3 ]
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Reference: [1] Patent: US4705892, 1987, A,
  • 3
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Reference: [1] Synthetic Communications, 1985, vol. 15, # 14, p. 1277 - 1290
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  • [ 75-29-6 ]
  • [ 2508-29-4 ]
  • [ 40447-21-0 ]
Reference: [1] Farmaco, 1995, vol. 50, # 1, p. 47 - 54
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  • [ 2508-29-4 ]
  • [ 24424-99-5 ]
  • [ 75178-87-9 ]
YieldReaction ConditionsOperation in experiment
100% at 0 - 20℃; for 2.5 h; The amino alcohol 21b (1.0 equiv, 2.87 mmol, 0.30 mL) was dissolved in 3 mL of CH2Cl2 ([21b] =0.5 mL/L), cooled in an ice bath and Boc2O (1.0 equiv, 2.87 mmol, 0.63 mL) was added. After stirring for 0.5 h at 0 °C, the cooling bath was removed and the mixture was allowed to stir for 2 h at ambient temperature. Subsequently, 3 mL of 1 N HCl solution (aq.) were added, the phases were separated,the organic layer was washed successively with 1 N HCl-, saturated NaHCO3 solution in water and brine/H2O 1:1 (each 3 mL) and dried over MgSO4. After concentration with 2 mL of chloroform under reduced pressure for two times and drying in high vacuum under stirring for 0.5 h delivered the carbamate 12c (2.99 mmol, quant., 567 mg) as a colorless oil.
Reference: [1] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 369 - 383
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YieldReaction ConditionsOperation in experiment
98% With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; N-t-Boc-5 -amino- 1-pentanol. To a 1.0 L one-neck round-bottom flask containing a solution of 5 -amino- 1-pentanol (15.0 g, 145.4 mmol) in water (140 mL) and saturated aqueous NaHCC>3 (1.4 mL), a solution of di-tert-butyl dicarbonate (33.3 g, 152.7 mmol) in THF (280 mL) was added. The mixture was then stirred at room temperature overnight with the flask open to the atmosphere. The reaction mixture was diluted with saturated aqueous NaHCC>3 (90 mL) and extracted with EtOAc (400 mL). The organic layer was separated, dried over Na2S04, filtered, and the solvent was evaporated providing 28.9 g (98percent) of the final product as clear colorless oil. 'll NMR analysis showed the product was clean of impurities, and no further purification was attempted. Alternatively, N-t-Boc-5- amino- 1-pentanol can be obtained from TCI America of Portland, OR.
98% at 0 - 20℃; for 4 h; Step 1: Synthesis of tert-butyl 5-hydroxypentylcarbamate (AU)[0558] To a stirred solution of 5-aminopentan-l-ol (AT, 3.1 g, 30.05 mmol) in dichloromethane (30 mL) was added di-tert-butyl dicarbonate (6.56 g, 30.06 mmol) at 0 °C. The resulting mixture was then stirred at rt for 4h. The solvent was removed under reduced pressure to give a crude residue which was purified by flash silica gel chromatography (eluent: ethyl acetate/petroleum ether (v:v= 1: 2)) to give AU (yield: 98percent) as a colorless oil. LC-MS (ES+): m/z 204.00 [MH+], tR=1.29 min (2.6 minute run).
98% With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; N-t-Boc-5-amino-l-pentanol. To a 1.0 L one-neck round-bottom flask containing a solution of 5-amino-l -pentanol (15.0 g, 145.4 mmol) in water (140 mL) and saturated aqueous NaHC03 (1.4 mL), a solution of di-tert-butyl dicarbonate (33.3 g, 152.7 mmol) in THF (280 mL) was added. The mixture was then stirred at room temperature overnight with the flask open to the atmosphere. The reaction mixture was diluted with saturated aqueous NaHC03 (90 mL) and extracted with EtOAc (400 mL). The organic layer was separated, dried over Na2S04, filtered, and the solvent was evaporated providing 28.9 g (98percent) of the final product as clear colorless oil. NMR analysis showed the product was clean of impurities, and no further purification was attempted. Alternatively, N-t-Boc-5-amino-l-pentanol can be obtained from TCI America of Portland, OR.
98% at 0 - 20℃; for 4 h; To a stirred solution of 5-aminopentan-1-ol (AT, 3.1 g, 30.05 mmol) in dichloromethane (30 mL) was added di-tert-butyl dicarbonate (6.56 g, 30.06 mmol) at 0° C.
The resulting mixture was then stirred at rt for 4 h.
The solvent was removed under reduced pressure to give a crude residue which was purified by flash silica gel chromatography (eluent: ethyl acetate/petroleum ether (v:v=1:2)) to give AU (yield: 98percent) as a colorless oil. LC-MS (ES+): m/z 204.00 [MH+], tR=1.29 min (2.6 minute run).
98% at 0 - 20℃; for 4 h; Step 1:
Synthesis of tert-butyl 5-hydroxypentylcarbamate (AU)
To a stirred solution of 5-aminopentan-1-ol (AT, 3.1 g, 30.05 mmol) in dichloromethane (30 mL) was added di-tert-butyl dicarbonate (6.56 g, 30.06 mmol) at 0° C.
The resulting mixture was then stirred at room temperature for 4 hours.
The solvent was removed under reduced pressure to give a crude residue which was purified by flash silica gel chromatography (eluent: ethyl acetate/petroleum ether (v:v=1:2)) to give AU (yield: 98percent) as a colorless oil. LC-MS (ES+): m/z 204.00 [MH+], tR=1.29 min (2.6 minute run).
95% 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).
93.1% at 20℃; Cooling with ice To a solution of 41 (20 g, 194 mmol) in DCM (0.2 L) was added (Boc)20 dropwise (42.3 g, 194 mmol) under an ice bath. The reaction was stirred at RT over night. Then the mixture solution was extracted with DCM and washed with water. The combined organic layers were washed with saturated NaCl, dried over Na2S04, and filtered. The solvent was removed in vacuum to give 42 as an oil (37 g, yield 93.1 percent). XH NMR (300 MHz, CDC13) δ: 3.5(m, 2H), 3.2 (m, 2H), 1.6-1.5(m, 4H), 1.4-1.3(m, 1 1H).
83% With dmap; triethylamine In chloroform at 20℃; for 3 h; 5-Amino-1-pentanol (30, 2 g, 19 mmol), Boc2O (4.5 g, 20 mmol), Et3N (2.1 g, 21 mmol), DMAP (0.23 g, 1.9 mmol) and CHCl3 (20 mL) were placed in a 100 mL reaction flask. The reaction mixture was allowed to stir for 3 h at rt. After the volatile materials were removed under reduced pressure, the resulting reside was purified by flash column chromatography (CHCl3) to yield 31. To a flame-dried 100 mL round-bottom flask containing a magnetic stirring bar were charged 31 (30 mmol), Et3N (30 mmol), DMAP (3 mmol), and CHCl3 (30 mL). The solution was cooled to 0 °C, and TsCl (30 mmol) dissolved in CHCl3 was added to the solution over 10 min. The reaction mixture was stirred at rt for 3 h. After all the volatile materials were removed under reduced pressure, the crude residue was purified by flash column chromatography (CHCl3) to get 32. 31: 83percent; 1H NMR (300 MHz, CDCl3): δ 3.63 (2H, m, CH2N), 3.11 (2H, m, CH2OH), 1.61–1.39 (15H, m, 3×CH2, –C(CH3)3).
74% With potassium carbonate In methanol; water at 20℃; for 2 h; A mixture of 5-amino-1-pentanol (3.0 g, 29.1 mmol), t-Boc anhydride (6.1 g, 34.9 mmol), and K2CO3 (4 g) in 50/50 water/methanol (25 mL) was stirred at ambient temperature for 2 h. The reaction mixture was quenched with water (25 mL) and extracted with EtOAc (2x25 mL). Combined extracts were washed with water and brine, dried (MgSO4), and filtered. Solvent removal gave the product as a viscous colourless oil (4.4 g, 74percent). 1H NMR (CDCl3): δ ppm 1.3–1.63 (m, 15H), 3.07–3.18 (m, 2H), 3.65 (t, J = 6.44 Hz, 2H), 4.55 (br s, 1H). 13C NMR (CDCl3): δ ppm 22.89, 28.38, 29.80, 32.20, 40.39, 62.53. 79.07, 156.08. HRMS (ESI+) m/z calcd for [M+H]+ C10H22NO3 204.15997, found 204.16070.

Reference: [1] Synthesis, 1990, p. 366 - 368
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 17, p. 7892 - 7901
[3] Tetrahedron Letters, 1992, vol. 33, # 20, p. 2833 - 2836
[4] Carbohydrate Research, 1999, vol. 322, # 3-4, p. 201 - 208
[5] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 3, p. 1376 - 1392
[6] Patent: WO2016/27262, 2016, A1, . Location in patent: Page/Page column 68
[7] Patent: WO2015/17519, 2015, A1, . Location in patent: Paragraph 000222
[8] Patent: WO2016/118666, 2016, A1, . Location in patent: Paragraph 0556; 0557; 0558
[9] Patent: WO2016/118697, 2016, A1, . Location in patent: Paragraph 270
[10] Patent: US2018/72711, 2018, A1, . Location in patent: Paragraph 0377; 0378
[11] Patent: US2018/99940, 2018, A1, . Location in patent: Paragraph 0791-0792
[12] Journal of Medicinal Chemistry, 2007, vol. 50, # 21, p. 5217 - 5226
[13] Bioconjugate Chemistry, 2018,
[14] Patent: US5679708, 1997, A,
[15] Angewandte Chemie - International Edition, 2012, vol. 51, # 32, p. 8110 - 8113
[16] Tetrahedron, 1998, vol. 54, # 28, p. 7955 - 7976
[17] Journal of the American Chemical Society, 2003, vol. 125, # 51, p. 15935 - 15940
[18] Molecules, 2013, vol. 18, # 11, p. 13957 - 13978
[19] Angewandte Chemie - International Edition, 2005, vol. 44, # 15, p. 2275 - 2279
[20] Patent: WO2013/116682, 2013, A1, . Location in patent: Paragraph 00223
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[22] Analytical Chemistry, 1998, vol. 70, # 8, p. [d]1629-1638
[23] Organic and Biomolecular Chemistry, 2011, vol. 9, # 11, p. 4108 - 4115
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[25] Journal of Materials Chemistry B, 2014, vol. 2, # 10, p. 1344 - 1353
[26] Journal of Medicinal Chemistry, 2014, vol. 57, # 11, p. 4924 - 4939
[27] European Journal of Medicinal Chemistry, 2014, vol. 82, p. 16 - 35
[28] Chemistry - A European Journal, 2016, vol. 22, # 9, p. 3009 - 3018
[29] Journal of Medicinal Chemistry, 2014, vol. 57, # 22, p. 9673 - 9686
[30] Chemistry - A European Journal, 2013, vol. 19, # 5, p. 1762 - 1768
[31] Journal of the American Chemical Society, 2013, vol. 135, # 17, p. 6396 - 6398
[32] Advanced Synthesis and Catalysis, 2014, vol. 356, # 10, p. 2321 - 2329
[33] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 14, p. 4351 - 4357
[34] Organic Letters, 2015, vol. 17, # 24, p. 6054 - 6057
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[36] Tetrahedron Letters, 1996, vol. 37, # 19, p. 3379 - 3382
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YieldReaction ConditionsOperation in experiment
100% at 20℃; Cooling with ice To a stirred solution of 5-aminopentan-1-ol (13-1, 947.1 mg, 9.2 mmol) in CH2Cl2 (36 mL) was added Boc2O solution (4.2 mL, (18.3 mmol) in 10 mL of CH2Cl2) on ice. After being stirred at room temperature for 30 min, the reaction mixture was diluted with CHCl3, washed with aqueous saturated NaHCO3, and concentrated in vacuo. The residue was subjected to flash column chromatography (SiO2, n-hexane/EtOAc = 4:1, and then CHCl3/MeOH = 10:1) to obtain 13-2 (1.97 g, quant). 1H NMR (500 MHz, CDCl3) δ 4.58 (broad s, 1H), 3.63 (borad t, J = 6.0 Hz, 2H), 3.11 (broad q, J = 7.0 Hz, 2H), 1.60-1.55 (m, 2H), 1.53-1.47 (m, 2H), 1.43 (s, 9H), 1.40-1.35 (m, 2H); HRMS (ESI, positive) m/z 226.1388 [M+Na]+ (calcd for C10H21NO3 226.1414).
100% at 20℃; for 2 h; Inert atmosphere 5-Aminopentan-1-ol (5.0 g, 48.47 mmol)and di-tert-butyl dicarbonate (12.69g, 58.16 mmol) were dissolved in anhydrous DCM (25 mL) and stirred undernitrogen for 2 h. Water (15 mL) was added and the product was extracted in DCM(3 x 20 mL). The combined organic extracts were sequentially washed with aq NaHCO3and brine, dried over MgSO4, filtered, and concentrated to give theproduct as colorless oil (9.85 g, 100percent). 1H NMR (CDCl3)  d 3.62 (m, 2H), 3.11 (m, 2H), 1.62-1.31 (m, 15H).13C NMR (75 MHz, CDCl3) d  155.9, 79.5, 62.8,41.8, 31.9, 29.9, 28.4, 22.7. IR: 3341, 2934, 1687, 1527, 1169 cm-1. MS m/z (ESI) 204.20 (M+ +1).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 6, p. 1608 - 1611
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 9, p. 2808 - 2811
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YieldReaction ConditionsOperation in experiment
95% With triethylamine In tetrahydrofuran; dichloromethane; chloroform EXAMPLE 31
5-(N-t-Boc)-amino-1-pentanol
A solution of (t-Boc)2O (21.8 g, 100 mmol) in anhydrous THF (100 mL) was added to a solution of 5-aminopentan-1-ol (10.3 g, 100 mmol) and Et3N (30.3 g, 300 mmol) in anhydrous THF (20 mL) at 0° C.
The resulting solution was stirred at rt overnight.
The solvent was evaporated, and the residue was dissolved in CHCl3.
The solution was washed with brine, dried (Na2SO4), and concentrated.
The residue was purified by flash chromatography on a silica gel column using CH2Cl2 and then 20:1 CH2Cl2-MeOH as eluents to give 19.3 g (95percent) of the title compound as a pale yellow oil.
1H NMR (CDCl3) δ 1.50-1.80 (m, 6H), 2.57-2.85 (m, 8H), 3.85 (s, 4H), 3.94 (s, 2H), 3.95 (s, 2H), 7.08 (d, 2H, J=7.4 Hz), 7.57 (d, 2H, J=7.5 Hz).
13C NMR (CDCl3) δ 26.04, 26.76, 26.98, 47.51, 47.76, 47.96, 48.08, 49.27, 53.84, 54.06, 120.48, 120.69, 136.73, 157.86, 158.15, 158.84. HRMS (FAB) m/z 369.2758 (M+H)+(C21H33N6 requires 369.2767).
Reference: [1] Patent: US6191273, 2001, B1,
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YieldReaction ConditionsOperation in experiment
71% With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; To a stirred mixture of 5-amino-1 -pentanol (48.5 mmol, 5.0 g) and sodium bicarbonate (145.4 mmol, 12.2 g) in water (26 mL) at 05C, a solution of benzyl chloroformate (63.1 mmol, 9.0 mL) in anh THF (26 mL) was added dropwise. After stirring at room temperature overnight, reaction mixture was diluted with EtOAc and H20. The organic layer was separated, washed with brine (2x30 mL), dried over anh MgS04, filtered and solvent removed under reduced pressure. The crude was dispersed in the minimum amount of cyclohexane and the resulting solid was filtered and dried under vacuum. The title compound was obtained as a white solid (8.2 g, 71 percent). 1 H NMR (400 MHz, CDCI3) δ 7.35 (m, 5H), 5.09 (2H, s), 4.8 (1 H, brs), 3.65 (2H, m), 3.20 (2H, m), 1 .50-1 .58 (6H, m), 1 .39 (2H, m).
70% With sodium hydroxide In water at 20℃; for 22 h; To a stirred solution of 5-aminopentanol S1 (6.00 g, 0.058 mol, 1.0 eq.) in 1 M aq. NaOH (65 mL) was added CbzCl (9.1 mL, 0.064 mol, 1.1 eq.) in a dropwise fashion. The reaction mixture was stirred at room temperature for 22 h during which time a white precipitate formed. The reaction mixture was filtered in vacuo and washed with water (20 mL) to afford the crude product which was purified by recrystallisation (EtOAc/c-Hex) affording S2 (9.67 g, 70 percent) as a white solid. Rf = 0.2 (c-Hex/EtOAc; 1:1); IR (NaCl, dep. from CH2Cl2) 3320, 2935, 1692, 1543, 1455, 1375, 1272, 1053, 1028 cm-1; HRMS (ESI): calcd. for [C13H19NO3 + Na]+ 260.1263, found 260.1258; 1H NMR (CDCl3, 400 MHz): d 1.33 – 1.47 (m, 2H), 1.48 – 1.65 (m, 4H), 3.21 (app. q, J = 6.4 Hz, 2H), 3.64 (t, J = 6.4 Hz, 2H), 4.78 (br s, 1H), 5.09 (s, 2H), 7.28 – 7.40 (m, 5H) ppm; 13C NMR (CDCl3, 100 MHz): d 22.9 (CH2), 29.8 (CH2), 32.2 (CH2), 40.9 (CH2), 62.7 (CH2), 66.6 (CH2), 128.1 (CH), 128.1 (CH), 128.5 (CH), 136.6 (C), 156.4 (C) ppm. Data are consistent with those reported in literature.
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Reference: [1] Synthesis, 1991, # 9, p. 713 - 716
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Reference: [1] Tetrahedron, 2000, vol. 56, # 43, p. 8433 - 8441
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  • [ 83948-54-3 ]
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[7] Journal of Medicinal Chemistry, 2018, vol. 61, # 17, p. 7892 - 7901
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