Diisopropylethylamine → 4-nitrophenyl tetrahydro-2H-pyran-4-ylcarbamate

HRID 589847Notes

Reaction equation

HRID 589847 reaction equation
Cl.[O:2]1[CH2:7][CH2:6][CH:5]([NH2:8])[CH2:4][CH2:3]1.Cl[C:10]([O:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=[O:11].C(N(C(C)C)CC)(C)C.C(=O)([O-])O.[Na+]>ClCCl>[O:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:10](=[O:11])[O:12][C:13]2[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 516892Sodium BicarbonateHCID 441186934-Aminotetrahydropyran hydrochloride

Product 1

HCID 665843044-nitrophenyl tetrahydro-2H-pyran-4-ylcarbamateYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.00 g (36.3 mmol) of tetrahydro-2H-pyran-4-yl-amine hydrochloride (CAS 38041-19-9) in 300 ml of dichloromethane, cooled to −15° C. are added portionwise 13.2 g (65.4 mmol) of 4-nitrophenyl chloroformate (CAS 7693-46-1) and then 12.7 ml (72.7 mmol) of diisopropylethylamine. Stirring is continued at −0° C. for 2 hours, and 20 ml of saturated aqueous sodium hydrogen carbonate solution are then added. The organic phase is separated out by settling and dried over sodium sulfate and the solvent is evaporated off under reduced pressure. The residue is purified by chromatography on a column 80 g of silica gel, eluting with a mixture of 20% acetone in dichloromethane, to give 8.26 g of 4-nitrophenyl tetrahydro-2H-pyran-4-ylcarbamate in the form of a white powder.

Workup

  1. customThe organic phase is separated out
  2. dry with materialdried over sodium sulfate
  3. customthe solvent is evaporated off under reduced pressure
  4. customThe residue is purified by chromatography on a column 80 g of silica gel
  5. washeluting with a mixture of 20% acetone in dichloromethane

Sources & evidence

ORD record
ord-69da2b72d66e44d18b5b1c97af2ed335
Source dataset
uspto-grants-2016_01
Patent number
US09233965B2

Reaction notes

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