Carbon Tetrachloride → HCID 86598335, compound

HRID 1270413Notes

Reaction equation

HRID 1270413 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([C:13]([N:15]2[C@H:20]([CH2:21][C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][CH:23]=3)[CH2:19][N:18]3[C@@H:31]([CH2:34]O)[CH2:32][CH2:33][C@@H:17]3[CH2:16]2)=[O:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:58]>C(#N)C>[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([C:13]([N:15]2[C@H:20]([CH2:21][C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][CH:23]=3)[CH2:19][N:18]3[C@@H:31]([CH2:34][Cl:58])[CH2:32][CH2:33][C@@H:17]3[CH2:16]2)=[O:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 9936657HCID 9936657, compound

Product 1

HCID 86598335HCID 86598335, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of (3,5-bis(trifluoromethyl)phenyl)-[(3R,6R,8aR)-6-hydroxymethyl-3-(1H-indol-3-ylmethyl)-hexahydropyrrolo[1,2-a]pyrazin-2-yl]-methanone (1.30 g), triphenylphosphine (1.2 g), carbontetrachloride (4 mL), and acetonitrile (40 mL) was heated at 70° C. for 6 hours. After cooling to room temperature the solvent was removed in vacuo. The residue was purified by ion-exchange chromatography on a strong cation exchange (SCX) column, to afford 3,5-bis(trifluoromethyl)phenyl-[(3R,6R,8aR)-6-chloromethyl-3-(1H-indol-3-ylmethyl)-hexahydropyrrolo[1,2-a]pyrazin-2-yl]-methanone (1.06 g) (Intermediate 5).

Workup

  1. temperatureAfter cooling to room temperature the solvent
  2. customwas removed in vacuo
  3. customThe residue was purified by ion-exchange chromatography on a strong cation exchange (SCX) column

Sources & evidence

ORD record
ord-f2db1eddb3a34837a4baae98847c0b97
Source dataset
uspto-grants-2007_04
Patent number
US07202238B2

Reaction notes

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