Water → HCID 59512477, compound

HRID 1158429Notes

Reaction equation

HRID 1158429 reaction equation
[CH:1]1([NH:4][CH2:5][CH:6]2[CH2:11][CH2:10][CH2:9][CH2:8][O:7]2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:19][C:20](Cl)([O:22]C(=O)OC(Cl)(Cl)Cl)Cl.O>C1COCC1.CN(C)C1C=CN=CC=1>[CH:1]1([N:4]([CH2:5][CH:6]2[CH2:11][CH2:10][CH2:9][CH2:8][O:7]2)[C:20]([Cl:19])=[O:22])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 94429TriphosgeneHCID 43403632HCID 43403632, compound

Product 1

HCID 59512477HCID 59512477, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of cyclopropyl-(tetrahydro-pyran-2-ylmethyl)-amine (200 mg, 0.74 mmol) in THF (4 mL) is added triethylamine (144 μL, 1.036 mmol) and 4-dimethylaminopyridine (1.81 mg, 0.015 mmol). The mixture is cooled to 0° C., and triphosgene (88 mg, 0.296 mmol) is added in one portion. After stirring for 30 min at 0° C. and overnight at RT, water is cautiously added and the solution is extracted with AcOEt. The combined organic extracts are washed with brine, dried over Na2SO4, filtered and concentrated. TLC, Rf (CH2Cl2/MeOH 95:5)=0.9.

Workup

  1. extractionthe solution is extracted with AcOEt
  2. washThe combined organic extracts are washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-42951f5f58cb4384a6a5fc03a4290bda
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

Loading…