Triethylamine → HCID 86647411, compound

HRID 1948382Notes

Reaction equation

HRID 1948382 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH:10]([OH:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16](=N)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([N:14]=[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C@H:10]([OH:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 136809Benzophenone imineHCID 21874161tert-Butyl 4-amino-3-hydroxypiperidine-1-carboxylate

Product 1

HCID 86647411HCID 86647411, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-butyl-4-amino-3-hydroxypiperidine-1-carboxylate (11.9 g; 55 mmol) and benzophenone imine (10 g; 59 mmol; 1.05 eq.) were dissolved in anhydrous toluene and heated to reflux for 18 hrs. Monitored the reaction by TLC (30% EtOAc/hexanes with 0.1% triethylamine). The crude reaction was concentrated and purified by flash column chromatography. Isolation gave 18.4 g of the title compound in an 86% yield. LC/MS (ES+)[(M+H)+]: 381 for C23H28N2O3.

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 hrs
  3. customThe crude reaction
  4. concentrationwas concentrated
  5. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-7500a834f0364033aa1e0cf740d80605
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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