4-FORMYL-N-CBZ-PIPERIDINE synthesis
- Product Name:4-FORMYL-N-CBZ-PIPERIDINE
- CAS Number:138163-08-3
- Molecular formula:C14H17NO3
- Molecular Weight:247.29
79-37-8
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$17.67/10gm:
122860-33-7
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$5.00/1g
138163-08-3
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$6.00/1g
Yield:138163-08-3 100%
Reaction Conditions:
with triethylamine in dichloromethane;dimethyl sulfoxide
Steps:
26.c 26c.
26c. Phenylmethyl 4-formylpiperidinecarboxylate To a stirred solution of oxalyl chloride (2M solution in dichloromethane, 10.9 mL, 21.9 mmol) was added DMSO (3.1 mL, 3.4 g, 43.8 mmol) in dichloromethane (6 mL) over a period of 15 minutes. The product of Example 26b (4.4 g, 17.5 mmol) in dichloromethane (7 mL) was then added at -78° C. over a period of 15 minutes. The resultant solution was stirred at -78° C. for 1 hour and then triethylamine (12.2 mL, 8.86 g, 87.5 mmol) was added, dropwise, over a period of 15minutes. The mixture was further stirred at -78° C. for 30 min and then at 0° C. for 15 min. The reaction mixture was quenched with water and extracted with dichloromethane. The combined organic phase was washed with 1% HCl, water, dried over sodium sulfate, filtered and evaporated to give the title compound (4.4 g, 100%) which was used in the next step without purification. 1H NMR (300 MHz, CDCl3) δ9.65 (s, 1H), 7.28-7.38 (m, 5H), 5.12 (s, 2H), 4.04 (br d, J=13.1 Hz, 2H), 2.97-3.06 (m, 2H), 2.38-2.45 (m, 1H), 1.88-1.92 (m,2H), 1.52-1.64 (m, 2H). 13C NMR (75 MHz, CDCl3) δ202.7, 155.2, 136.7, 128.5, 128.6, 127.9, 67.2, 47.8, 43.0, 25.1. LRMS (APIMS) m/z 248 (MH+).
References:
Fang, Xinqin;Garvey, David S.;Gaston, Ricky D.;Lin, Chia-En;Ranatunga, Ramani R.;Richardson, Stewart K.;Wang, Tiansheng;Wang, Weiheng;Wey, Shiow-Jyi US2003/203915, 2003, A1
122860-33-7
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$5.00/1g
138163-08-3
189 suppliers
$6.00/1g
138163-07-2
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$5.00/5g
138163-08-3
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$6.00/1g
160809-38-1
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$38.00/1g
138163-08-3
189 suppliers
$6.00/1g
148148-48-5
38 suppliers
$92.00/1g
138163-08-3
189 suppliers
$6.00/1g