2-(Methylamino)ethanol → HCID 57516933, compound

HRID 1944861Notes

Reaction equation

HRID 1944861 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:37][NH:38][CH2:39][CH2:40]O.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:37][NH:38][CH2:39][CH2:40][O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 80162-(Methylamino)ethanolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 11831452tert-butyl N-(2-(4-hydroxyphenyl)ethyl)carbamate

Product 1

HCID 57516933HCID 57516933, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-Boc-tyramine (750 mg, 3.16 mmol) and triphenylphosphine (1.655 g, 6.308 mmol) in THF (30 mL) was added 2-(methylamino)ethanol (0.38 mL, 4.75 mmol) followed by DIAD (1.25 mL, 6.31 mmol). After stirring at room temperature for 72 h, the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (gradient elution 1:20 to 1:3 MeOH/DCM) to afford the title compound (407 mg, 44%) as an oily white solid. ES/MS calcd. for C16H27N2O3+ 295.2. Found m/z=295.2 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel (gradient elution 1:20 to 1:3 MeOH/DCM)

Sources & evidence

ORD record
ord-9f6f030e413b421a9ed5b9c946de8449
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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