Diisobutylaluminum hydride → HCID 86695166, compound

HRID 1504012Notes

Reaction equation

HRID 1504012 reaction equation
[Cl:1][C:2]1[C:3]2[C:4]3[CH2:5][CH:6]([CH2:15][C:16](OCC)=[O:17])[CH2:7][CH2:8][C:9]=3[S:10][C:11]=2[N:12]=[CH:13][N:14]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[Cl:1][C:2]1[C:3]2[C:4]3[CH2:5][CH:6]([CH2:15][CH2:16][OH:17])[CH2:7][CH2:8][C:9]=3[S:10][C:11]=2[N:12]=[CH:13][N:14]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 86695165HCID 86695165, compound

Product 1

HCID 86695166HCID 86695166, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 2-[3-chloro-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-12-yl]acetate (2.88 g, 9.27 mmol, 1.00 equiv) in 25 mL of distilled THF was added DIBAL-H (25% in hexane, 10.56 g, 2.00 equiv) dropwise at −30° C. under nitrogen. The resulting solution was stirred for 2 h at this temperature and quenched with saturated aqueous NH4Cl, extracted with 3×100 mL of ethyl acetate. The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1) to afford 2.20 g (88%) of the desired 2-[3-chloro-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-12-yl]ethan-1-ol as a light yellow solid. MS: m/z 269, 270 [M+H]+.

Workup

  1. customquenched with saturated aqueous NH4Cl
  2. extractionextracted with 3×100 mL of ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-157e47ca4555499f98e3e20794c62719
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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