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[ CAS No. 38175-35-8 ]

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Chemical Structure| 38175-35-8
Chemical Structure| 38175-35-8
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CAS No. :38175-35-8 MDL No. :MFCD09027613
Formula : C11H15NO Boiling Point : 285.6±33.0°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :177.24 g/mol Pubchem ID :12937991
Synonyms :

Safety of [ 38175-35-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 38175-35-8 ]

  • Upstream synthesis route of [ 38175-35-8 ]
  • Downstream synthetic route of [ 38175-35-8 ]

[ 38175-35-8 ] Synthesis Path-Upstream   1~4

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YieldReaction ConditionsOperation in experiment
77% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 65℃; for 2 h; In an oven-dried three neck flask was added 4-(3-methoxyphenyl)pyrrolidin-2-one (7) (3.66 g, 19.2 mmol) and THF (50 ml). The mixture was cooled to 0°C (ice-salt bath) and LiAlH4 (16.0 ml of a 2.4 M solution in THF, 38.4 mmol) was carefully added dropwise. The resulting mixture was allowed to gradually warm to RT and heated at 65°C for 2h. The mixture was then cooled to 0°C (ice-salt bath) and slowly quenched by the dropwise addition of 0.5 M NaOH (~4.5 ml). The quenched mixture was filtered through a 7-8 cm pad of celite and the filter-cake was washed with CH2Cl2 (200 mL). The filtrate was dried (anhydrous Na2SO4), filtered and concentrated. The residue was purified by simple distillation (Kugelrhor) (100 C 2.7 mmHg) to afford 2.60 g (77percent yield) of racemic pyrrolidine 8 as colorless oil: 1H NMR (400 MHz, CDCl3) δ 7.20 (t, J = 7.88 Hz, 1H), 6.82 (bd, J = 8.40 Hz, 1H), 6.78 – 6.76 (m, 1H), 6.73 (dd, J = 8.16, 2.58 Hz, 1H), 3.78 (s, 3H), 3.34 (dd, J = 10.79, 7.62 Hz, 1H), 3.18 (quint, J = 8.20 Hz, 1H), 3.16 – 3.03 (m, 3H), 2.84 (dd, J = 10.50, 8.30 Hz, 1H), 2.57 (bs (1H), 2.25 – 2.17 (m, 1H), 1.89 – 1.79 (m, 1H). 13C NMR (100 MHz, CDCl3) δ 159.76, 145.96, 129.51, 119.65, 113.32, 111.24, 55.25, 52.15, 47.45, 45.71 34.48. LCMS (50-95percent acetonitrile in 0.05percent TFA over 10 minutes) retention time = 6.08 min, ESI m/z = 178, [M+H]+. HRMS ESI-TOF (m/z) = 178.1245 (178.1232 calculated for C11H15NO2) [M + H]+.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 10, p. 1897 - 1902
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 10, p. 1897 - 1902
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 10, p. 1897 - 1902
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 10, p. 1897 - 1902
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