Ethanolamine → HCID 86713720, compound

HRID 1406055Notes

Reaction equation

HRID 1406055 reaction equation
Cl[CH2:2][C@@H:3]([OH:11])[CH2:4][C:5]#[C:6][Si:7]([CH3:10])([CH3:9])[CH3:8].[NH2:12][CH2:13][CH2:14][OH:15].CO>ClCCl>[OH:15][CH2:14][CH2:13][NH:12][CH2:2][C@@H:3]([OH:11])[CH2:4][C:5]#[C:6][Si:7]([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 887MethanolHCID 11084670HCID 11084670, compound

Product 1

HCID 86713720HCID 86713720, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (2S)-1-chloro-5-(trimethylsilyl)pent-4-yn-2-ol (80 g, 420 mmol) and 2-aminoethanol (110 g, 1.8 mol) was stirred at 80° C. for 18 hours. Silica gel chromatography (Gradient: 1% to 10% methanol in dichloromethane) provided the product as a yellow oil. Yield: 30 g, 140 mmol, 33%. 1H NMR (400 MHz, CD3OD) δ 3.80-3.88 (m, 1H), 3.61-3.72 (m, 2H), 2.84 (dd, J=12.3, 3.3 Hz, 1H), 2.69-2.81 (m, 2H), 2.64 (dd, J=12.0, 8.5 Hz, 1H), 2.45 (dd, half of ABX pattern, J=16.6, 5.5 Hz, 1H), 2.37 (dd, half of ABX pattern, J=16.6, 7.0 Hz, 1H), 0.12 (s, 9H).

Sources & evidence

ORD record
ord-bd517275b1ab47c698af4dcaad1bdee8
Source dataset
uspto-grants-2014_12
Patent number
US08916564B2

Reaction notes

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