Ethanolamine → HCID 68386798, compound

HRID 1771933Notes

Reaction equation

HRID 1771933 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([C:14]([OH:16])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[CH2:50]([CH2:52][NH2:53])[OH:51]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([C:14](=[O:16])[NH:53][CH2:52][CH2:50][OH:51])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 6951168(3S)-1-((tert-butoxy)carbonyl)piperidine-3-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 68386798HCID 68386798, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(S)-Piperidine-1,3-dicarboxylic acid 1-tert-butyl ester (500 mg, 2.2 mmol), HATU (833 mg, 2.2 mmol) and Di-isopropylethylamine (761 μL, 4.4 mmol) were stirred in dry DCM (10 ml) in an ice bath for 5 min, then at room temperature for 5 min. Ethanolamine (198 μL, 3.28 mmol) was added and the reaction stirred at room temperature for 3 hrs. The reaction was diluted with DCM (40 ml), washed with water (50 ml), the DCM layer separated and dried (MgSO4) and concentrated. The residue was columned on silica (20 g isolute). Eluting: MeOH/DCM 0-5% 5 CV, MeOH/DCM 5%-5% 10 CV, MeOH/DCM 5-10% 5 CV. TLC visualized with KMnO4. This yielded the product as a clear oil (327 mg).

Workup

  1. washwashed with water (50 ml)
  2. customthe DCM layer separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. washEluting

Sources & evidence

ORD record
ord-f8621dbe28394fd0b25fc7300635c1f0
Source dataset
uspto-grants-2016_02
Patent number
US09249155B2

Reaction notes

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