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

HRID 2238349Notes

Reaction equation

HRID 2238349 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].C(=O)(O)[O-].[Na+].[CH:10]1[C:22]2[CH:21]([CH2:23][O:24][C:25](Cl)=[O:26])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH:13]=[CH:12][CH:11]=1>O1CCCC1.O>[CH:10]1[C:22]2[CH:21]([CH2:23][O:24][C:25](=[O:26])[NH:4][CH2:3][CH2:1][OH:2])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 700EthanolamineHCID 343679-Fluorenylmethyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 2817739(9H-fluoren-9-yl)methyl N-(2-hydroxyethyl)carbamateYield 52.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of ethanolamine (0.49 g, 8 mmol), tetrahydrofuran, water and sodium bicarbonate (1.5 g, 18 mmol) at 6° C., was added a solution 9-fluorenylmethylchloroformate (2.27 g, 8.8 mmol) in tetrahydrofuran in one portion, stirring was continued for 1 h allowing the mixture to warm to room temperature. The mixture was diluted with water and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate filtered and evaporated to a crude product. The crude product was re-crystallised from dichloromethane to give (2-hydroxy-ethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester as a white solid (1.2 g).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to a crude product
  5. customThe crude product was re-crystallised from dichloromethane

Sources & evidence

ORD record
ord-2437c5aa6f314b68a318f378916906c8
Source dataset
uspto-grants-2010_05
Patent number
US07718767B2

Reaction notes

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