Ammonia → HCID 59134341, compound

HRID 2425372Notes

Reaction equation

HRID 2425372 reaction equation
[Na].N.C([N:10]1[C:18]2[C:13](=[CH:14][C:15]3[O:22][C:21]([CH3:24])([CH3:23])[CH:20]([OH:25])[CH:19]([NH:26][C:27]4C=CC(OCC)=C[CH:28]=4)[C:16]=3[CH:17]=2)[CH2:12][C:11]1=[O:36])C1C=CC=CC=1.[Cl-].[NH4+]>C1COCC1>[C:13]1([CH2:28][CH2:27][NH:26][CH:19]2[C:16]3[CH:17]=[C:18]4[C:13]([CH2:12][C:11](=[O:36])[NH:10]4)=[CH:14][C:15]=3[O:22][C:21]([CH3:24])([CH3:23])[CH:20]2[OH:25])[CH:14]=[CH:15][CH2:16][CH2:17][CH:18]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 67245776HCID 67245776, compound

Product 1

HCID 59134341HCID 59134341, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen stream, sodium (90 mg, 3.91 mmol) was added to liquid ammonia (5 mL) at −78° C., and the resulting mixture was stirred. A solution of 1-benzyl-7-hydroxy-6,6-dimethyl-8-phenetylamino-3,6,7,8-tetrahydro-1H-pyrano[2,3-f]indole-2-one (173 mg, 0.39 mmol) in THF (2 mL) was added dropwise at −45° C., and the resulting mixture was stirred for 15 minutes. Upon the completion of the reaction, saturated ammonium chloride aqueous solution was added thereto, the resulting solution was extracted with ethyl acetate. The resulting organic phase was washed with water and then with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, concentrated and purified by silica gel column (ethyl acetate) to obtain the aimed product (yield: 19%).

Workup

  1. stirringthe resulting mixture was stirred for 15 minutes
  2. additionwas added
  3. extractionthe resulting solution was extracted with ethyl acetate
  4. washThe resulting organic phase was washed with water
  5. dry with materialwith saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. custompurified by silica gel column (ethyl acetate)

Sources & evidence

ORD record
ord-da18f304b8914dd6a9381278d1b2251a
Source dataset
uspto-grants-2011_06
Patent number
US07964623B2

Reaction notes

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