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[ CAS No. 1147557-97-8 ]

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Chemical Structure| 1147557-97-8
Chemical Structure| 1147557-97-8
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CAS No. :1147557-97-8 MDL No. :MFCD15071431
Formula : C11H19NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :213.27 g/mol Pubchem ID :52987765
Synonyms :

Safety of [ 1147557-97-8 ]

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 [ 1147557-97-8 ]

  • Upstream synthesis route of [ 1147557-97-8 ]
  • Downstream synthetic route of [ 1147557-97-8 ]

[ 1147557-97-8 ] Synthesis Path-Upstream   1~8

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  • [ 1211586-09-2 ]
Reference: [1] Patent: WO2016/90079, 2016, A1,
[2] Patent: EP3281942, 2018, A1,
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  • [ 1211526-53-2 ]
Reference: [1] Patent: CN105646318, 2016, A,
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  • [ 1181816-12-5 ]
Reference: [1] Organic Letters, 2009, vol. 11, # 16, p. 3523 - 3525
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YieldReaction ConditionsOperation in experiment
100% With sodium tetrahydroborate In methanol at 0℃; for 0.5 h; Inert atmosphere Step 8 terf-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate [00179] To a solution of ferf-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate (507 mg, 2.4 mmol) in MeOH (5.0 mL) was added NaBH4 (182 mg, 4.8 mmol) at 0 °C under N2. It was stirred at 0 °C for 30 min. The solution was concentrated by evaporator in vacuo to give crude solid. A saturated solution of NaHCO3 (30 mL) was added. The aqueous mixture was extracted with DCM (4x30 mL). The combined organic solution was dried over anhydrous Na2SO4 and then concentrated by evaporation in vacuo to afford terf-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate (5 mg, 100percent) as a white solid. [00180] 1HNMR (300 MHz, CDCI3): δ 4.18 (m, 1 H), 3.88 (d, 4 H), 2.53 (m, 2 H), 2.08 (m, 2 H), 1.42 (s, 9 H).
95% With sodium tetrahydroborate In methanol at 20℃; for 1 h; Tert-Butyl tert-butyl tert-butyl tert-butyl tert-butyl t-butyl-6-oxo-2-azaspiro [3.3] heptane-2-carboxylate (0.23 g, 1.1 mmol, 1 eq)To the methanol (8 mL), sodium borohydride (0.12 g, 3.2 mmol, 2.9 eq) was added in portions and reacted at room temperature for 1 h. After the reaction, water (20 mL) was added and extracted with EA (20 mL x 2) The residue was dried over sodium sulf
93.7% at 0 - 25℃; for 1 h; Inert atmosphere Tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate (4.22 g, 20 mmol) was added in methanol (30 mL), cooled under nitrogen gas protection to 0°C, and sodium borohydride (1.52 g, 40 mmol) was added.
After addition, the reaction solution was heated to 25°C and stirred for 1 h, after completing reaction as measured by LC-MS, water (1 mL) was added to quench reaction, solvent was removed by vacuum distillation, water (100 mL) and ethyl acetate (100 mL) were added, the phases were separated, the organic phase was washed with hydrochloric acid (1 mol/L, 50 mL), dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated to obtain the title compound in white color (4.0 g, yield 93.7 percent).
89.2% With sodium tetrahydroborate In ethyl acetate at 0 - 20℃; for 0.666667 h; t-Butyl 2-oxo-6-azaspiro[3.3]heptane-6-carboxylate (2.00 g, 9.47 mmol) was dissolvedin EtOAc (40 mL). The mixture was cooled to 0 °C, and sodium borohydride (548 mg, 14.19 mmol) was added in portions, the mixture was stirred for 10 min at 0 °C, and then further stirredat rt for 30 min. The mixture was cooled to 0 °C, and quenched with saturated aqueousammonium chloride (2.0 mL). The mixture was stirred for 30 min, water (20 mL) and ethylacetate (50 mL) were added, and the mixture was stirred for 10 min. After the mixture waspartitioned, the water phase was extracted with ethyl acetate (100 mL x 2). The combined organicphases were washed with saturated aqueous NaCl and dried over anhydrous sodium sulfate, andfiltered. The filtrate was concentrated in vacuo to get the title compound as an off-white solid(1.80 g, 89.2percent).MS (ESI, pos. ion) m/z:236.1 [M+Ht

Reference: [1] Patent: WO2013/13308, 2013, A1, . Location in patent: Paragraph 00178-00180
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 13, p. 5663 - 5672
[3] Patent: CN106565706, 2017, A, . Location in patent: Paragraph 0179; 0180; 0181
[4] Patent: EP3281942, 2018, A1, . Location in patent: Paragraph 0105; 0106
[5] Patent: WO2018/133858, 2018, A1, . Location in patent: Paragraph 00221
[6] Patent: US2012/129830, 2012, A1, . Location in patent: Page/Page column 13
[7] Tetrahedron, 2016, vol. 72, # 46, p. 7268 - 7275
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Reference: [1] Tetrahedron, 2016, vol. 72, # 46, p. 7268 - 7275
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Reference: [1] Organic Letters, 2009, vol. 11, # 16, p. 3523 - 3525
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  • [ 934664-41-2 ]
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Reference: [1] Patent: US2012/129830, 2012, A1,
[2] Patent: CN106565706, 2017, A,
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Reference: [1] Patent: CN106565706, 2017, A,
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