Diglycolamine → HCID 57357491, compound

HRID 1244180Notes

Reaction equation

HRID 1244180 reaction equation
C(O[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])(C)(C)C.[NH2:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][OH:19]>C(Cl)(Cl)Cl>[C:6]([CH:14]([NH2:13])[CH2:15][O:16][CH2:17][CH2:18][OH:19])([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:12]

Participants

4

Reactant 2

HCID 13578DiglycolamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 57357491HCID 57357491, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of di-tert-butylcarbonate (10.27 g, 47.2 mmol) in chloroform (40 mL) was added to a solution of 2-(2-aminoethoxy)-ethanol (5.0 g, 47.62 mmol) in chloroform (40 mL) and the mixture was stirred at room temperature for 1.5 hrs. The solution was washed with water (30 mL), the organic layer dried (MgSO4), and concentrated in vacuo to give 2-(2-Boc-aminoethoxy)-ethanol (9.6 g, 99%). 1H NMR (300 MHz, CDCl3) δ 5.43 (s, 1H), 3.43 (s, 1H), 3.56 (mn, 4H), 3.73 (t, 2H, J=5.4 Hz), 3.32 (m, 2H), 1.45(s, 9H); 13C NMR (67.8 MHz, CDCl3) δ 156.06, 79.06, 77.18, 72.14, 70.08, 61.31, 40.21, 28.21.

Workup

  1. washThe solution was washed with water (30 mL)
  2. dry with materialthe organic layer dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7b7cdbd23e594e2a992b1a1e87d70e08
Source dataset
uspto-grants-2006_10
Patent number
US07122189B2

Reaction notes

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