Aluminium lithium hydride → (3R,6S)-6-benzhydryl-tetrahydropyran-3-ol

HRID 1897931Notes

Reaction equation

HRID 1897931 reaction equation
[CH:1]([C@@H:14]1[CH2:20][C@@H:19]2[C@@H:17]([O:18]2)[CH2:16][O:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCCCC>[CH:1]([C@H:14]1[O:15][CH2:16][C@H:17]([OH:18])[CH2:19][CH2:20]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54762329(1S,4S,6R)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane

Product 1

HCID 11514547(3R,6S)-6-benzhydryl-tetrahydropyran-3-ol

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent2×

Procedure

(1S,4S,6R)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane 28a (0.3 g, 1.13 mmol) in dry pentane (10 ml) was added to a suspension of LiAlH4 (0.21 g, 5.64 mmol) in dry pentane (20 ml). The resulting reaction mixture was stirred under N2 for 20 hr at room temperature, and then quenched with 10% NaOH, diluted with ethyl acetate (30 ml), and the precipitate removed by filtration. The organic phase was washed with brine and dried over anhydrous Na2SO4. Removal of solvent followed by flash chromatography of the crude product produced pure (3R,6S)-6-benzhydryl-tetrahydro-pyran-3-ol, 33a, 0.23 g (75%, [α]D=(−)−61.6, c=1, MeOH).

Workup

  1. customThe resulting reaction mixture
  2. customquenched with 10% NaOH
  3. additiondiluted with ethyl acetate (30 ml)
  4. customthe precipitate removed by filtration
  5. washThe organic phase was washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-430441fa111649d586873d4f42c6ba7c
Source dataset
uspto-grants-2013_08
Patent number
US08519159B2

Reaction notes

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