Triethylamine → HCID 22631805, compound

HRID 1369205Notes

Reaction equation

HRID 1369205 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)=[O:3].C(N(CC)CC)C.[NH2:22][CH2:23][CH2:24][CH2:25][OH:26]>C1COCC1>[N+:12]([C:9]1[CH:10]=[CH:11][C:6]([CH2:5][O:4][C:2]([NH:22][CH2:23][CH2:24][CH2:25][OH:26])=[O:3])=[CH:7][CH:8]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

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

Product 1

HCID 22631805HCID 22631805, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension stirred under argon at room temperature of 4-nitrobenzyl chloroformate (5 g, 23 mmol) and triethylamine (6.4 mL, 46 mmol) in THF (25 mL) was added 3-amino-1-propanol (1.9 mL, 26 mmol). The resulting mixture was stirred for 72 hr. then was concentrated. The residue was purified by chromatography on silica gel (0.5-2% MeOH/CH2Cl2) to give the title compound (2 g, 34%) as a pale yellow oil: MS (ES) 255.3 (M+H)+.

Workup

  1. concentrationthen was concentrated
  2. customThe residue was purified by chromatography on silica gel (0.5-2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-7f57463df5494a09984e6e6d23f846c4
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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