1-Boc-4-[methoxy(methyl)carbamoyl]piperidine synthesis
- Product Name:1-Boc-4-[methoxy(methyl)carbamoyl]piperidine
- CAS Number:139290-70-3
- Molecular formula:C13H24N2O4
- Molecular Weight:272.34
6638-79-5
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84358-13-4
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139290-70-3
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Yield: 100%
Reaction Conditions:
Stage #1:N,O-dimethylhydroxylamine*hydrochloride;N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid with triethylamine in DMF (N,N-dimethyl-formamide) at 20; for 0.166667 h;
Stage #2: with benzotriazol-1-ol;1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in DMF (N,N-dimethyl-formamide)
Stage #3: with hydrogenchloride in water
Steps:
3
To a stirring suspension of t-Boc-isonipecotic acid (19) (2.34 g, 10.2 mmol) and the Weinreb amine (1.5 g, 15 mmol) in DMF (50 mL), was added triethylamine (2.8 mL, 20 mmol) at room temperature. After stirring for 10 min, HOBt (1.62 g, 12 mmol) was added, followed by EDCI (2.3 g, 12 mmol). The resulting solution was stirred overnight and concentrated. The residue was taken up in 1 N HCl (100 mL) and extracted with EtOAc (3×100 mL). The combined organic extracts were washed with sat NaHCO3 (50 mL), brine (50 mL), dried (MgSO4) and concentrated to obtain a colorless oil (20) (2.79 g, >100%). 1H NMR (500 MHz, CDCL3) δ4.14 (m, 2H), 3.71 (s, 3H), 3.19 (s, 3H), 2.78 (m, 3H), 1.68 (m, 4H), 1.46 (s, 9H); MS (ESI+) m/z 217.72 (M+H+-isobutylene).
References:
Myriad Pharmaceuticals, Inc. US2004/14763, 2004, A1 Location in patent:Page 21
84358-13-4
395 suppliers
$5.00/5g
139290-70-3
186 suppliers
$6.00/100mg
6638-79-5
586 suppliers
$6.00/25g
139290-70-3
186 suppliers
$6.00/100mg
84358-13-4
395 suppliers
$5.00/5g
1117-97-1
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inquiry
139290-70-3
186 suppliers
$6.00/100mg
142851-03-4
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$5.00/1g
1117-97-1
73 suppliers
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139290-70-3
186 suppliers
$6.00/100mg