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[ CAS No. 203662-51-5 ]

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2D
Chemical Structure| 203662-51-5
Chemical Structure| 203662-51-5
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Product Details of [ 203662-51-5 ]

CAS No. :203662-51-5MDL No. :MFCD09910310
Formula : C13H23NO3 Boiling Point : 318.135°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :241.33Pubchem ID :21955339
Synonyms :

Computed Properties of [ 203662-51-5 ]

TPSA : 49.8 H-Bond Acceptor Count : 3
XLogP3 : 1.9 H-Bond Donor Count : 1
SP3 : 0.77 Rotatable Bond Count : 4

Safety of [ 203662-51-5 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 203662-51-5 ]

  • Upstream synthesis route of [ 203662-51-5 ]
  • Downstream synthetic route of [ 203662-51-5 ]

[ 203662-51-5 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 79099-07-3 ]
  • [ 106-95-6 ]
  • [ 203662-51-5 ]
YieldReaction ConditionsOperation in experiment
99.9% With ammonium chloride; zinc In tetrahydrofuran; water at -10 - 40℃; a, compound 1 ( 50g, 0.25mol) and zinc powder (49.2g, 0 . 75mol) tetrahydrofuran and ammonium chloride aqueous solution suspended (2/3,500 ml) in a mixed solution. - 10-10°C to control the temperature, to the reaction solution adding dropwisely compound 2 ( 109.3g, 0 . 90mol). The reaction slowly increase 15-40°C, to continue reaction 2-5 hours. TLC (petroleum ether/ethyl acetate = 2/1 volume ratio) display reaction is ended. The reaction solution with ethyl acetate (100mLx3). Combined with the phase, by sodium sulfate drying, filtering after concentration to obtain crude product is distilled under reduced pressure. The crude product by silica gel column (petroleum ether/ethyl acetate = 30/1 volume ratio to 10/1) to obtain colorless oily compound 3 ( 60g), yield 99.9percent.
95%
Stage #1: With ammonium chloride; zinc In tetrahydrofuran at 10℃; Industry scale
Stage #2: With sulfuric acid; water In tetrahydrofuranIndustry scale
Stage #3: With sodium hydrogencarbonate In tetrahydrofuran; water; <i>tert</i>-butyl alcoholIndustry scale
tert-butyl 4-allvl-4-hvdroxypiperidine-1-carboxvlate tert-butyl 4-oxopiperidine-i-carboxylate (1000 g, 5.02 mol) was dissolved in allylbromide (1080 ml_, 12.4 mol, 2.5 eq), THF (1000 ml_) and saturated ammonium chloride solution (5000 ml_). The reaction was cooled to 10 0C and zinc dust (650 g, 10 mol, 2 eq) was added portion wise. After addition the reaction mixture was stirred overnight. TLC was taken (heptane/EtOAc 7:1 ) and showed full conversion. The reaction mixture was diluted with water (5 L) and acidified with 10percent H2SO4 to pH~6. The reaction mixture was extracted with MTBE (3x). The organic layers were combined and extracted with saturated solution of NaHCO3, brine and evaporated to give tert-butyl 4-allyl-4-hydroxypiperidine-1-carboxylate (1153 g, 95percent).
Reference: [1] Patent: CN105440046, 2016, A, . Location in patent: Paragraph 0006
[2] Patent: WO2010/58318, 2010, A1, . Location in patent: Page/Page column 25-26
[3] Patent: WO2014/139144, 2014, A1, . Location in patent: Page/Page column 165
[4] Patent: US2014/288081, 2014, A1, . Location in patent: Paragraph 0667; 0668; 0669
[5] Patent: WO2014/139325, 2014, A1, . Location in patent: Page/Page column 178; 179
[6] Journal of the American Chemical Society, 2015, vol. 137, # 36, p. 11586 - 11589
  • 2
  • [ 79099-07-3 ]
  • [ 1730-25-2 ]
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YieldReaction ConditionsOperation in experiment
19.08% at 0℃; for 3 h; Inert atmosphere 1-Tert-butoxycarbonyl-4-piperidone (2.5 g, 12.55 mmol) was dissolved in anhydrous tetrahydrofuran (25 mL), allyl magnesium bromide (1M, 16.30 mL) was slowly added dropwise under nitrogen atmosphere at 0° C. over 1 h. The reaction was stirred for 2 h at 0° C. until the reaction was complete as monitored by TLC. The reaction mixture was quenched with saturated aqueous solution of ammonium chloride (80 mL), the reaction was allowed to warm to room temperature and extracted with ethyl acetate (100 mL). The organic phase was washed with saturated aqueous solution of sodium chloride (100 mL) once and dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under vacuum. The residue was purified with column chromatography (height: 100 mm, diameter: 50 mm, 100-200 silica gel, petroleum ether/ethyl acetate=4/1, 2/1) to afford 3-hydroxy-3-(1-tert-butoxycarbonyl-4-piperidyl)-1-propene (750.00 mg, 3.11 mmol, yield: 19.08percent) as a yellow liquid. 1H NMR (400 MHz, CHLOROFORM-d:) δ 5.93-5.83 (m, 1H), 5.27-5.14 (m, 2H), 3.83 (br. s., 2H), 3.18 (br. s., 2H), 2.25 (d, J=7.5 Hz, 2H), 1.61-1.50 (m, 4H), 1.48 (s, 9H).
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 48, p. 6457 - 6459
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 9, p. 3672 - 3683
[3] Patent: US2018/148452, 2018, A1, . Location in patent: Paragraph 0191
[4] Patent: US2012/252778, 2012, A1, . Location in patent: Paragraph 0334-0335
[5] Patent: WO2018/26371, 2018, A1, . Location in patent: Paragraph 0320
  • 3
  • [ 79099-07-3 ]
  • [ 106-95-6 ]
  • [ 203662-51-5 ]
YieldReaction ConditionsOperation in experiment
45% With zinc In tetrahydrofuran Step A
1-(t-Butoxycarbonyl)-4-(prop-2-enyl)-4-hydroxypiperidine
A dry round bottom flask was purged with nitrogen and charged with 1-t-butoxycarbonyl-4-piperidinone (20 g, 100 mmol), titanocene dichloride (1.2 g, 5 mmol) and zinc dust (7.8 g, 120 mmol) in 100 mL dry THF. Allyl bromide (11.3 mL, 130 mmol) was added and the mixture was stirred for 5 h at rt.
The mixture was diluted with 700 mL EtOAc, washed with 2.0 M HCl (2*200 ML), 100 mL of sat'd NaCl, dried over MgSO4 and concentrated.
Flash chromatography (650 g silica, 10/1 CH2Cl2/Et2O eluant) afforded 10.9 g (45percent) of the title compound: 1H NMR (300 MHz) δ 1.4-1.6 (13H), 2.2-2.25 (d, 2H), 3.1-3.2 (m, 2H), 3.75-3.85 (m, 2H), 5.1-5.25 (m, 2H), 5.78-5.92 (m, 1H).
Reference: [1] Patent: US6265434, 2001, B1,
  • 4
  • [ 79099-07-3 ]
  • [ 1730-25-2 ]
  • [ 203662-51-5 ]
Reference: [1] Patent: US6498159, 2002, B1,
  • 5
  • [ 10049-21-5 ]
  • [ 79099-07-3 ]
  • [ 1730-25-2 ]
  • [ 203662-51-5 ]
Reference: [1] Patent: US6518423, 2003, B1,
  • 6
  • [ 203662-51-5 ]
  • [ 240401-09-6 ]
YieldReaction ConditionsOperation in experiment
35%
Stage #1: With sodium periodate In water; <i>tert</i>-butyl alcohol at 50℃; for 0.5 h; Industry scale
Stage #2: With sodium disulfite In water; <i>tert</i>-butyl alcohol at 20 - 50℃; for 59 h; Industry scale
tert-butyl (3RS)-3-hydroxy-1-oxa-8-azaspiro[4.5ldecane-8-carboxylate tert-butyl 4-allyl-4-hydroxypiperidine-1-carboxylate (1153 g, 4.8 mol) was dissolved in tert-butanol (10 L) and water (4 L). To the solution sodium periodate (1124 g, 5.3 mol, 1.1 eq) was added and the mixture was stirred at 50 0C for 30 minutes. At 50 0C a solution of Na2S2O5 (1007 g, 5.3 mol, 1.1 eq) in water (4.2 L) was added dropwise over 4 hours to the solution. After addition the reaction mixture was stirred for 7 hours at 50 0C and another 48 hours at RT. The mixture was transferred to an extraction vessel and the organic layer was separated from the aqueous layer. The aqueous layer was extracted (3x) with ethyl acetate. The organic layers were combined and washed with a saturated solution of Na2S2O3 (3x) to give a colorless solution. The solution was washed with brine and evaporated to give crude product (987 g, 80percent). The crude product was purified by flash chromatography (10-80percent EtOAc/Heptane) to give the title compound (287 g, 35percent). m/z 158 (MH+ minus Boc).
Reference: [1] Patent: WO2010/58318, 2010, A1, . Location in patent: Page/Page column 26
  • 7
  • [ 203662-51-5 ]
  • [ 954236-44-3 ]
Reference: [1] Patent: WO2018/26371, 2018, A1,
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