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[ CAS No. 240401-09-6 ]

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2D
Chemical Structure| 240401-09-6
Chemical Structure| 240401-09-6
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Product Details of [ 240401-09-6 ]

CAS No. :240401-09-6MDL No. :MFCD09749842
Formula : C13H23NO4 Boiling Point : 391°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :257.33Pubchem ID :22744549
Synonyms :

Computed Properties of [ 240401-09-6 ]

TPSA : 59 H-Bond Acceptor Count : 4
XLogP3 : 0.8 H-Bond Donor Count : 1
SP3 : 0.92 Rotatable Bond Count : 2

Safety of [ 240401-09-6 ]

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

Application In Synthesis of [ 240401-09-6 ]

  • Upstream synthesis route of [ 240401-09-6 ]
  • Downstream synthetic route of [ 240401-09-6 ]

[ 240401-09-6 ] Synthesis Path-Upstream   1~5

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YieldReaction ConditionsOperation in experiment
96% at 0 - 23℃; for 2.00 h; Inert atmosphere Sodium borohydride (445 mg, 11.8 mmol) was added to a 0° C. solution of tert-butyl 3-oxo-1-oxa-8-azaspiro[4.5]decane-8-carboxylate (1.50 g, 5.88 mmol) in methanol (59 mL) and the reaction mixture was stirred at 23° C. for 2 hours.
After removal of solvent in vacuo, the residue was partitioned between ethyl acetate and water.
The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide a mixture of C74 and C75 as a colorless oil.
Yield of racemic product: 1.45 g, 5.63 mmol, 96percent. GCMS m/z 257.1 [M+].
1H NMR (400 MHz, CDCl3) δ 4.54-4.48 (br m, 1H), 3.93 (dd, half of ABX pattern, J=10.2, 4.3 Hz, 1H), 3.85-3.79 (m, 1H), 3.67-3.53 (br m, 2H), 3.40-3.28 (m, 2H), 1.97 (dd, half of ABX pattern, J=13.7, 6.2 Hz, 1H), 1.89-1.48 (m, 6H, assumed; partially obscured by water peak), 1.46 (s, 9H). A portion of this racemic material (1.30 g, 5.05 mmol) was separated into its component enantiomers via supercritical fluid chromatography [Column: Phenomenex Lux Amylose-1, 5 μm; Mobile phase: 85:15 carbon dioxide/(methanol containing 0.2percent ammonium hydroxide)]. (0402) The first-eluting product, obtained as a gum that exhibited a negative (−) rotation, was designated as C74. Yield: 650 mg, 2.53 mmol, 50percent for the separation. The second-eluting product, obtained as a solid that exhibited a positive (+) rotation, was designated as C75. Yield: 620 mg, 2.41 mmol, 48percent for the separation. The indicated absolute stereochemistries of C74 and C75 were assigned on the basis of conversion of C74 to C72 (see step 4).
96% With sodium tetrahydroborate In methanol at 0 - 23℃; for 2.00 h; Sodium borohydride (445 mg, 11.8 mmol) was added to a 0° C. solution of tert-butyl 3-oxo-1-oxa-8-azaspiro[4.5]decane-8-carboxylate (1.50 g, 5.88 mmol) in methanol (59 mL) and the reaction mixture was stirred at 23° C. for 2 hours. After removal of solvent in vacuo, the residue was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide a mixture of C32 and C33 as a colorless oil. Yield of racemic product: 1.45 g, 5.63 mmol, 96percent. GCMS m/z 257.1 [M+]. 1H NMR (400 MHz, CDCl3) δ 4.54-4.48 (br m, 1H), 3.93 (dd, half of ABX pattern, J=10.2, 4.3 Hz, 1H), 3.85-3.79 (m, 1H), 3.67-3.53 (br m, 2H), 3.40-3.28 (m, 2H), 1.97 (dd, half of ABX pattern, J=13.7, 6.2 Hz, 1H), 1.89-1.48 (m, 6H, assumed; partially obscured by water peak), 1.46 (s, 9H).
Reference: [1] Patent: US2018/208607, 2018, A1. Location in patent: Paragraph 0226; 0384; 0400-0402
[2] Patent: US2018/208608, 2018, A1. Location in patent: Paragraph 0322; 0339
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 21, p. 6545 - 6553
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YieldReaction ConditionsOperation in experiment
48%
Stage #1: With borane-THF In tetrahydrofuran at 0 - 20℃; for 1.00 h;
Stage #2: With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran; water at 0 - 20℃; for 18.00 h;
Borane-tetrahydrofuran-complex solution in tetrahydrofuran (16. 7mL, 1M. 16. 7MMOL) was added to a solution of tert-butyl 1-oxa-8-azaspiro [4.5] dec-3-ene-8- carboxylate (from step (iv) above; 2g, 8. 37MMOL) in tetrahydrofuran (25mL) at 0°C. After lh at room temperature, a mixture of 35 percent w/w hydrogen peroxide solution (6ML, ca. 67mmol) and 4 M sodium hydroxide solution (17mL) was slowly added at 0°C. Then the reaction mixture was stirred at room temperature for 18h before it was partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with saturated sodium sulfite solution, then brine and finally dried over magnesium sulfate, filtered and concentrated to give the crude mixture of products as a colourless oil. The mixture was separated by flash chromatography on silica gel, eluting with a gradient solvent system of 50-100 percent ethyl acetate in hexane, then 1-2 percent methanol in ethyl acetate to furnish 1.03g of the title compound (48 percent). H NMR (360 MHz, CDC13) : 8 4.51-4. 49 (1H, m), 3.92 (1H, dd, J4. 4, 10. LHZ), 3. 84- 3.79 (1H, m), 3.59 (1H, br s), 3.38-3. 30 (1H, m) 1.96 (1H, dd, J 6. 3,13. 6Hz), 1. 85- 1.79 (2H, m), 1.73-1. 63 (2EI, m), 1. 58-1. 50 (2H, m), 1.45 (9H, s).
Reference: [1] Patent: WO2004/78750, 2004, A1. Location in patent: Page 88-89
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YieldReaction ConditionsOperation in experiment
35%
Stage #1: With sodium periodate In water; <i>tert</i>-butyl alcohol at 50℃; for 0.50 h; Industry scale
Stage #2: With sodium disulfite In water; <i>tert</i>-butyl alcohol at 20 - 50℃; for 59.00 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
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Reference: [1] Patent: US6498159, 2002, B1
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Reference: [1] Patent: WO2018/26371, 2018, A1
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