Ethanolamine → (9H-fluoren-9-yl)methyl N-(2-hydroxyethyl)carbamate

HRID 1449429Notes

Reaction equation

HRID 1449429 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].[CH:5]1[C:17]2[CH:16]([CH2:18][O:19][C:20](Cl)=[O:21])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1.N1C=CC=CC=1>ClCCl>[CH:5]1[C:17]2[CH:16]([CH2:18][O:19][C:20]([NH:1][CH2:2][CH2:3][OH:4])=[O:21])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 1049PyridineHCID 343679-Fluorenylmethyl chloroformate

Product 1

HCID 2817739(9H-fluoren-9-yl)methyl N-(2-hydroxyethyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Aminoethanol (1.2 g, 19.7 mmol) in dry dichloromethane (5 ml) was added dropwise to a solution of 9-fluorenylmethylchloroformate (5.0 g, 19.3 mmol) together with pyridine (1.5 g, 19.4 mmol). The mixture was stirred for a total of 1.25 hours then diluted with dichloromethane (50 ml), washed with water (25 ml), a saturated solution of ammonium chloride (25 ml), the organic phase was separated dried over anhydrous magnesium sulphate, filtered and the filtrate evaporated in vacuo to give a white solid. This material was crystallised from dichloromethane to give 2-(9-fluorenylmethoxycarbonyl)aminoethanol.

Workup

  1. washwashed with water (25 ml)
  2. customa saturated solution of ammonium chloride (25 ml), the organic phase was separated
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customthe filtrate evaporated in vacuo
  6. customto give a white solid
  7. customThis material was crystallised from dichloromethane

Sources & evidence

ORD record
ord-d62cdf78789247babcad0b29fc24bc37
Source dataset
uspto-grants-1997_02
Patent number
US05599587

Reaction notes

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