Ammonium formate → HCID 19050034, compound

HRID 1780221Notes

Reaction equation

HRID 1780221 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[N:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH:26]([CH2:36][Cl:37])[C:12]2=[C:13]2[C:17]=1[NH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[C:14]2[C:22]([O:24][CH3:25])=[O:23])C1C=CC=CC=1.C([O-])=O.[NH4+]>O1CCCC1.[Pd]>[CH3:25][O:24][C:22]([C:14]1[C:13]2[C:17](=[C:9]([OH:8])[CH:10]=[C:11]3[N:28]([C:29]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:30])[CH2:27][CH:26]([CH2:36][Cl:37])[C:12]3=2)[NH:16][C:15]=1[C:18]([F:21])([F:20])[F:19])=[O:23]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 19050108Benzo[1,2-b:4,3-b′]dipyrrole-1,6(3H)-dicarboxylic acid, 8-(chloromethyl)-7,8-dihydro-4-(phenylmethoxy)-2-(trifluoromethyl)-, 6-(1,1-dimethylethyl) 1-methyl ester

Product 1

HCID 19050034HCID 19050034, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In 2.63 ml of tetrahydrofuran, was dissolved 106.7 mg (198 μmol) of methyl 5-benzyloxy-3-t-butoxycarbonyl-1-chloromethyl-7-trifluoromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate. Thereto, 64 mg of 10% palladium on carbon was added, and then 656.4 μl of 25% ammonium formate was added dropwise under ice cooling. The mixture was stirred for one hour, and then the reaction mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain methyl-3-t-butoxycarbonyl-1-chloromethyl-5-hydroxy-7-trifluoromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate in a yield of 87.9 mg (99%).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-04ba2c60962d4c158fd19f2d89d8f437
Source dataset
uspto-grants-1997_05
Patent number
US05629430

Reaction notes

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