Diphosgene → HCID 118037570, compound

HRID 715594Notes

Reaction equation

HRID 715594 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.[O:18]=[C:19](Cl)[O:20][C:21](Cl)(Cl)Cl.[O:26]1[CH2:31][CH2:30]C(O)[CH2:28][CH2:27]1>C1(C)C=CC=CC=1>[O:26]1[CH2:31][CH2:30][CH:21]([O:20][C:19]([NH:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])[CH2:6][CH2:7]2)=[O:18])[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 10426DiphosgeneHCID 74956Tetrahydro-4H-pyran-4-olHCID 178466404-Amino-1-N-Cbz-piperidine

Product 1

HCID 118037570HCID 118037570, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

Benzyl 4-aminopiperidine-1-carboxylate (100 mg) is dissolved in toluene (1 mL), treated dropwise with a solution of diphosgene (52 μL) in toluene (1 mL) and stirred for 12 hours at 80° C. Tetrahydro-2H-pyran-4-ol (41 μL) is added and the mixture is heated for 3 hours at 80° C. The mixture is partitioned between ethylacetate and saturated aqueous NH4Cl solution. The organic phase is dried (MgSO4) and concentrated. The residue is purified by HPLC on reversed phase to give the title compound. LC (method 1): tR=0.95 min; Mass spectrum (ESI+): m/z=363 [M+H]+.

Workup

  1. temperaturethe mixture is heated for 3 hours at 80° C
  2. customThe mixture is partitioned between ethylacetate and saturated aqueous NH4Cl solution
  3. dry with materialThe organic phase is dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue is purified by HPLC on reversed phase

Sources & evidence

ORD record
ord-8e63531bb23747b7a5a62b9716448a75
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

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