1-Carboxy-3,5,7-trihydroxyadamantane → 1-Hydroxymethyl-3,5,7-adamantanetriol

HRID 1936528Notes

Reaction equation

HRID 1936528 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[C:7]([C:10]12[CH2:20][C:14]3([OH:21])[CH2:15][C:16]([OH:19])([CH2:18][C:12]([OH:22])([CH2:13]3)[CH2:11]1)[CH2:17]2)(O)=[O:8]>O1CCCC1>[OH:8][CH2:7][C:10]12[CH2:11][C:12]3([OH:22])[CH2:13][C:14]([OH:21])([CH2:15][C:16]([OH:19])([CH2:18]3)[CH2:17]1)[CH2:20]2

Participants

4

Reactant 2

HCID 120393761-Carboxy-3,5,7-trihydroxyadamantaneHCID 21226445Aluminium lithium hydride

Product 1

HCID 120393791-Hydroxymethyl-3,5,7-adamantanetriol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5 In an atmosphere of nitrogen, 15 mmol of aluminum lithium hydride was suspended in 15 ml of tetrahydrofuran (THF). Thereafter, 10 mmol of 1-carboxy-3,5,7-adamantanetriol was gradually added to the mixture while keeping the temperature of the mixture at 10° C. or lower by using ice bath. After the temperature of the mixture had been brought back to room temperature, the mixture was refluxed for 16 hours, giving 1-hydroxymethyl-3,5,7-adamantanetriol.

Workup

  1. customat 10° C.
  2. customhad been brought back to room temperature
  3. temperaturethe mixture was refluxed for 16 hours

Sources & evidence

ORD record
ord-0746218812284ac38896886c8f556cd2
Source dataset
uspto-grants-2002_05
Patent number
US06391520B1

Reaction notes

Loading…