Triethylamine → HCID 22631805, compound

HRID 2416695Notes

Reaction equation

HRID 2416695 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].C(N(CC)CC)C.Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=[O:15]>C1COCC1>[N+:24]([C:21]1[CH:20]=[CH:19][C:18]([CH2:17][O:16][C:14]([NH:1][CH2:2][CH2:3][CH2:4][OH:5])=[O:15])=[CH:23][CH:22]=1)([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90863-Amino-1-propanolHCID 782054-Nitrobenzyl chloroformate

Product 1

HCID 22631805HCID 22631805, compoundYield 314.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution stirred under argon at room temperature of 3-amino-1-propanol (0.77 g, 1.1 mmol) and triethylamine (2.85 mL, 7 mmol) in THF (5 mL) was added a suspension of 4-nitrobenzyl chloroformate (2 g, 1 mmol) in THF (20 mL). The resulting mixture was allowed to stir at room temperature over the weekend, then was concentrated. The residue was purified by chromatography on silica gel (0%-2% MeOH/CH2Cl2) to give the title compound (0.80 g, 34%) as a pale yellow oil: MS (ES) m/e 254.3 (M+H)+.

Workup

  1. additionwas added
  2. concentrationwas concentrated
  3. customThe residue was purified by chromatography on silica gel (0%-2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-91c926b8d3d04498a0534d32d1dfe171
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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