Isopropenyl chloroformate → HCID 131733476, compound

HRID 2278996Notes

Reaction equation

HRID 2278996 reaction equation
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.C([O-])(O)=O.[Na+].Cl[C:15]([O:17][C:18]([CH3:20])=[CH2:19])=[O:16]>CCOC(C)=O>[CH2:19]=[C:18]([O:17][C:15](=[O:16])[NH:2][CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)[CH3:20]

Participants

5

Reactant 3

HCID 93846Isopropenyl chloroformateHCID 516892Sodium BicarbonateHCID 441186934-Aminotetrahydropyran hydrochloride

Product 1

HCID 131733476HCID 131733476, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A biphasic mixture of 4-aminotetrahydropyran hydrochloride (1.0 g, 7.27 mmol) in EtOAc (20 mL) and satd. NaHCO3 (20 mL) was treated with isopropenyl chloroformate (0.874 mL, 7.99 mmol), stirred at RT for 2 h and the layers separated. The aqueous layer was extracted with EtOAc (1×) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford prop-1-en-2-yl(tetrahydro-2H-pyran-4-yl)carbamate (1.2 g, 89%). 1H NMR (400 MHz, DMSO-d6): δ 7.48 (d, J=7.7 Hz, 1 H), 4.57 (d, J=7.9 Hz, 2 H), 3.80-3.78 (m, 2 H), 3.51-3.40 (m, 1 H), 3.33-3.25 (m, 2H), 1.83 (s, 3 H), 1.69 (m, 2 H), 1.43-1.32 (m, 2H).

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted with EtOAc (1×)
  3. washthe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-bf3433f2890c49679bcd25bbb4db4760
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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