Triethylamine → HCID 118037353, compound

HRID 715584Notes

Reaction equation

HRID 715584 reaction equation
[OH: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.C(N(CC)CC)C.[N:25]([CH:28]([CH3:30])[CH3:29])=[C:26]=[O:27]>O1CCCC1>[CH:28]([NH:25][C:26]([O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:6][CH2:7]1)=[O:27])([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61277Isopropyl isocyanateHCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylate

Product 1

HCID 118037353HCID 118037353, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Benzyl 4-hydroxypiperidine-1-carboxylate (65 μL), is dissolved in tetrahydrofurane (2 mL), treated with triethylamine (890 μL) and 2-isocyanatopropane (420 μL) and the mixture is stirred for 12 hours at 80° C. Then the mixture is partitioned between saturated aqueous NH4Cl solution and ethylacetate and the organic phase is washed with brine and dried (MgSO4). The solvents are evaporated in vacuo and the residue is purified by HPLC on reversed phase to give the title compound. LC (method 1): tR=1.01 min; Mass spectrum (ESI+): m/z=321 [M+H]+.

Workup

  1. customThen the mixture is partitioned between saturated aqueous NH4Cl solution and ethylacetate
  2. washthe organic phase is washed with brine
  3. dry with materialdried (MgSO4)
  4. customThe solvents are evaporated in vacuo
  5. customthe residue is purified by HPLC on reversed phase

Sources & evidence

ORD record
ord-34d25a9416644310abfa62331a2bfc7a
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

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