Sodium sulfate decahydrate → HCID 22611376, compound

HRID 843945Notes

Reaction equation

HRID 843945 reaction equation
[CH2:1]([O:8][C:9]1[CH:22]=[CH:21][CH2:20][C:19]2[C:18]3[C:13](=[C:14]([NH:23][C:24](OC(C)(C)C)=O)[CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:22]=[CH:21][CH2:20][C:19]2[C:18]3[C:13](=[C:14]([NH:23][CH3:24])[CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 22611352HCID 22611352, compound

Product 1

HCID 22611376HCID 22611376, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.37 gm (3.37 mMol) 7-benzyloxy-4-(t-butyloxycarbonyl)amino-10H-cyclohepta[7,6-b]indole in 15 mL tetrahydrofuran was added dropwise over 30 minutes to a suspension of 0.47 gm (12.4 mMol) lithium aluminum hydride in 30 mL tetrahydrofuran at 0OC. After the addition was complete, the reaction mixture was stirred for 30 minutes at room temperature and then for 4 hours at reflux. The reaction mixture was cooled to room temperature and then to it was added sodium sulfate decahydrate until no more gas evolution was observed. The resulting suspension was filtered and the filter cake washed with dichloromethane. The combined filtrates were concentrated under reduced pressure and the residue subjected to silica gel chromatography, eluting with 10% methanol in dichloromethane containing 0.5% ammonium hydroxide. Fractions containing product were combined and concentrated under reduced pressure to give 0.97 gm (90%) of the desired compound.

Workup

  1. additionAfter the addition
  2. temperaturefor 4 hours at reflux
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationThe resulting suspension was filtered
  5. washthe filter cake washed with dichloromethane
  6. concentrationThe combined filtrates were concentrated under reduced pressure
  7. washeluting with 10% methanol in dichloromethane containing 0.5% ammonium hydroxide
  8. additionFractions containing product
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6c511ada0dc941dc9704f4fb1bdbb186
Source dataset
uspto-grants-2002_04
Patent number
US06380201B1

Reaction notes

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