Carbon Tetrachloride → Benzo[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

HRID 1780220Notes

Reaction equation

HRID 1780220 reaction equation
[CH2:1]([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]O)[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])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:58]>C(#N)C>[CH2:1]([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:58])[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])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 19050064HCID 19050064, compound

Product 1

HCID 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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

104.1 Milligrams (0.2 mmol) of methyl 5-benzyloxy-3-t-butoxycarbonyl-1-hydroxymethyl-7-trifluoromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate, and 104.9 mg (0.4 mmol) of triphenylphosphine were suspended in 1 ml of anhydrous acetonitrile. Thereto 115.3 μl (1.2 mmol) of carbon tetrachloride was added dropwise. The mixture was stirred for 5 hours under atmosphere of argon. After removal of the solvent, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain methyl 5-benzyloxy-3-t-butoxycarbonyl-1-chloromethyl-7-trifluoromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate in a yield of 106.7 mg (99%).

Workup

  1. customAfter removal of the solvent
  2. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-07ae660ad7fa40938443fbdadfe324a0
Source dataset
uspto-grants-1997_05
Patent number
US05629430

Reaction notes

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