Water → HCID 117603758, compound

HRID 1481967Notes

Reaction equation

HRID 1481967 reaction equation
[CH2:1]([C:5]1([CH2:18]OS(C)(=O)=O)[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)[CH2:2][CH:3]=[CH2:4].[Li+].[B-](CC)(CC)CC.O>C1COCC1>[CH2:1]([C:5]1([CH3:18])[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10]1)[CH2:2][CH:3]=[CH2:4]

Participants

5

Reactant 3

HCID 962WaterHCID 23712863Lithium triethylborohydrideHCID 117603884HCID 117603884, compound

Product 1

HCID 117603758HCID 117603758, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl 4-(but-3-en-1-yl)-4-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate (17 g, 48.9 mmol) in THF (250 mL) was added 1M solution of Superhydride (98 mL, 98 mmol) in THF and the resulting mixture was refluxed for 3 h. After cooling to room temp water was added and the mixture was extracted with ether (2×200 mL), washed with brine (100 mL), dried (Na2SO4), filtered and concentrated. The residue was purified by Biotage (0-20% EtOAc/hexane) to afford tert-butyl 4-(but-3-en-1-yl)-4-methylpiperidine-1-carboxylate (3.5 g, 13.81 mmol, 28.2% yield). 1H NMR (500 MHz, CDCl3) δ 5.88-5.80 (m, 1H), 5.03 (dq, J=17.1, 1.7 Hz, 1H), 4.96 (ddt, J=10.2, 2.1, 1.1 Hz, 1H), 3.62-3.49 (m, 2H), 3.23 (ddd, J=13.4, 9.3, 3.8 Hz, 2H), 2.09-1.97 (m, 2H), 1.48 (s, 9H), 1.43-1.22 (m, 6H), 0.96 (s, 3H). LCMS (M+H)=254.2. 8 g of starting material was also recovered.

Workup

  1. temperaturethe resulting mixture was refluxed for 3 h
  2. additionwas added
  3. extractionthe mixture was extracted with ether (2×200 mL)
  4. washwashed with brine (100 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by Biotage (0-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-530aa43424ea4eb09c687d0a630091df
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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