Diisobutylaluminumhydride → (4R,9aR)-6-hydroxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

HRID 11924Notes

Reaction equation

HRID 11924 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]2[C:15](=[CH:16][CH:17]=1)[CH2:14][C@H:13]1[N:8]2[C@H:9]([CH3:25])[CH2:10][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:12]1)=O.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[C:21]([O:20][C:18]([N:11]1[CH2:10][C@@H:9]([CH3:25])[N:8]2[C@H:13]([CH2:14][C:15]3[C:7]2=[N:6][C:5]([CH2:3][OH:2])=[CH:17][CH:16]=3)[CH2:12]1)=[O:19])([CH3:23])([CH3:22])[CH3:24]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 67239630(4R,9aR)-4-Methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2,6-dicarboxylic acid 2-tert-butyl ester 6-methyl ester

Product 1

HCID 67238448(4R,9aR)-6-hydroxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl esterYield 67.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.2 g (12.1 mmol) (4R,9aR)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2,6-dicarboxylic acid 2-tert-butyl ester 6-methyl ester in 100 ml tetrahydrofuran was cooled to 0 deg C. and treated dropwise with 48.4 ml diisobutylaluminium hydride (48.4 mmol; 1M solution in THF). The cooling bath was removed and after 1 h at room temperature the reaction was quenched with a 10% aqueous potassium sodium tartrate solution and ethyl acetate was added. The two-phase system was filtered through a bed of dicalite speed plus; the filtrate was extracted with ethyl acetate and the organic phase was dried over magnesium sulfate. After filtration and evaporation the residue was purified by chromatography on silica gel (0.032–0.062 mm) with ethyl acetate as eluant to afford the desired product as a light yellow foam (67.3%).

Workup

  1. customThe cooling bath was removed and after 1 h at room temperature the reaction
  2. customwas quenched with a 10% aqueous potassium sodium tartrate solution and ethyl acetate
  3. additionwas added
  4. filtrationThe two-phase system was filtered through a bed of dicalite speed
  5. extractionthe filtrate was extracted with ethyl acetate
  6. dry with materialthe organic phase was dried over magnesium sulfate
  7. filtrationAfter filtration and evaporation the residue
  8. customwas purified by chromatography on silica gel (0.032–0.062 mm) with ethyl acetate as eluant

Sources & evidence

ORD record
ord-c4c8a7c4280e4f479284330e5332aff7
Source dataset
uspto-grants-2006_08
Patent number
US07098337B2

Reaction notes

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