Water → 2-[[(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

HRID 2404968Notes

Reaction equation

HRID 2404968 reaction equation
[NH2:1][C@H:2]1[C@@H:6]2[O:7][C:8]([CH3:11])([CH3:10])[O:9][C@@H:5]2[C@@H:4]([O:12][CH2:13][C:14](OCC)=[O:15])[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[NH2:1][C@H:2]1[C@@H:6]2[O:7][C:8]([CH3:10])([CH3:11])[O:9][C@@H:5]2[C@@H:4]([O:12][CH2:13][CH2:14][OH:15])[CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 70854858ethyl 2-{[(3aR,4S,6R,6aS)-6-amino-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]oxy}acetate

Product 1

HCID 99425962-[[(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanolYield 65.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)acetate (4.2 g, 16.2 mmol, 1.00 equiv.) in dry tetrahydrofuran (50 mL) was slowly added to a suspension of lithium aluminum hydride (1.23 g, 32.4 mmol, 2.00 equiv.) in tetrahydrofuran (50 mL). The mixture was heated at reflux for about 1 hour, and then water was added (2 mL). After the solids were collected by filtration, the solids were washed with tetrahydrofuran (50 mL) and then dried in vacuo to give the title product as a yellow oil (2.3 g, 65%). MS: m/z=218 (MH)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for about 1 hour
  3. filtrationAfter the solids were collected by filtration
  4. washthe solids were washed with tetrahydrofuran (50 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-cca83917731c4ae88525fa2e19200126
Source dataset
uspto-grants-2014_08
Patent number
US08802850B2

Reaction notes

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