Aluminium lithium hydride → rac-(1R*,8R*,9R*)-9-(2-Hydroxy-ethyl)-tricyclo[6.2.2.02,7]dodeca-2,4,6-trien-9-ol

HRID 1879349Notes

Reaction equation

HRID 1879349 reaction equation
C([O:5][C:6](=O)[CH2:7][C:8]1([OH:20])[CH2:17][CH:16]2[CH2:18][CH2:19][CH:9]1[C:10]1[C:15]2=[CH:14][CH:13]=[CH:12][CH:11]=1)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:5][CH2:6][CH2:7][C:8]1([OH:20])[CH2:17][CH:16]2[CH2:18][CH2:19][CH:9]1[C:10]1[C:15]2=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 70999528rac-(1R*,8R*,9R*)-(9-hydroxy-tricyclo[6.2.2.02,7]dodeca-2,4,6-trien-9-yl)-acetic acid tert-butyl ester

Product 1

HCID 70999516rac-(1R*,8R*,9R*)-9-(2-Hydroxy-ethyl)-tricyclo[6.2.2.02,7]dodeca-2,4,6-trien-9-olYield 81.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.6 g of rac-(1R*,8R*,9R*)-(9-hydroxy-tricyclo[6.2.2.02,7]dodeca-2,4,6-trien-9-yl)-acetic acid tert-butyl ester in 10 mL of THF was added to 15.3 mL of a 1M LiAlH4 solution in THF at −10° C. The mixture was stirred for 4 h while the temperature reached slowly 0° C. The reaction was quenched by addition of a 15% aq. NaOH solution. The mixture was diluted with EtOAc, washed with H2O, dried over MgSO4 and concentrated in vacuo to obtain 1.6 g of the desired compound as white solid.

Workup

  1. customreached slowly 0° C
  2. customThe reaction was quenched by addition of a 15% aq. NaOH solution
  3. additionThe mixture was diluted with EtOAc
  4. washwashed with H2O
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f1e96188c73d4d09be15136f0cc735a3
Source dataset
uspto-grants-2012_11
Patent number
US08314253B2

Reaction notes

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