tert-butyl (1R,2S)-3,3-difluoro-2-hydroxycyclohexylcarbamate synthesis
- Product Name:tert-butyl (1R,2S)-3,3-difluoro-2-hydroxycyclohexylcarbamate
- CAS Number:1109284-41-4
- Molecular formula:C11H19F2NO3
- Molecular Weight:251.27
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![Cyclohexanol, 2,2-difluoro-6-[[(1R)-1-phenylethyl]amino]-, (1S,6R)-](/CAS/20200401/GIF/1109284-39-0.gif)
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Yield:1109284-41-4 67%
Reaction Conditions:
with palladium hydroxide 10 wt. % on activated carbon;palladium on activated carbon;hydrogen in methanol at 50; under 2585.81 Torr; for 16 h;
Steps:
4 Step 4 - Tert-butyl N-[(1R,2S)-3,3-difluoro-2-hydroxy-cyclohexyl]carbamate
A mixture of (1S,6R)-2,2-difluoro-6-[[(1R)-1-phenylethyl]amino]cyclohexanol (1.50 g, 5.88 mmol), Boc2O (1.41 g, 6.46 mmol), Pd(OH)2/C (300 mg, 5.88 mmol, 10% wt) and Pd/C (300 mg, 10% wt) in methanol (30 mL) was stirred at 50 °C under hydrogen (50 psi) for 16 hours. On completion, the mixture was filtered and the cake was washed with methanol (20 mL). The filtrate and washing were combined and concentrated in vacuo. The residue was purified by column chromatography on silica gel (PE: EA = 20:1 to 5:1) to give the title compound (1.00 g, 67% yield) as white solid.1H NMR (400 MHz, CDCl3) d 4.72 - 4.58 (m, 1H), 3.76 - 3.63 (m, 1H), 3.61 - 3.47 (m, 1H), 3.11 (m, 1H), 2.24 - 2.12 (m, 1H), 2.08 - 1.99 (m, 1H), 1.80 - 1.59 (m, 3H), 1.46 (s, 9H), 1.40 - 1.30 (m, 1H).
References:
WO2020/113233,2020,A1 Location in patent:Paragraph 002998; 003005-003006
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1109284-40-3
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1109284-39-0
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![7-OXABICYCLO[4.1.0]HEPTAN-2-ONE](/CAS/GIF/6705-49-3.gif)
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![2,2-DIFLUORO-7-OXA-BICYCLO[4.1.0]HEPTANE](/CAS/GIF/1109284-38-9.gif)
1109284-38-9
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