Carbon Tetrachloride → HCID 86755416, compound

HRID 1108483Notes

Reaction equation

HRID 1108483 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[N:24]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][C@@H:22]([CH2:32]O)[C:12]2=[C:13]2[C:17]=1[NH:16][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:14]2)[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:54]>ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[N:24]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][C@@H:22]([CH2:32][Cl:54])[C:12]2=[C:13]2[C:17]=1[NH:16][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 86755417HCID 86755417, compound

Product 1

HCID 86755416HCID 86755416, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

256.5 mg (0.57 mmole) of methyl (1S)-5-benzyloxy-3-t-butoxycarbonyl-1-hydroxymethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-7-carboxylate and 297.4. mg (1.13 mmole) of triphenylphosphine were dissolved in 6 ml of anhydrous dichloromethane, 0.33 ml (3.40 mmole) of carbon tetrachloride was added to the resulting solution, and the resulting mixture was stirred under argon atmosphere in the dark for 2 hours. The solvent was evaporated from the reaction mixture to give a residue, which was then purified by silica gel column chromatography using an eluate of hexane:ethyl acetate (4:1), followed by crystallization from hexane to give 245.3 mg of methyl (1S)-5-benzyloxy-3-t-butoxycarbonyl-1-chloromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-7-carboxylate. Yield, 92%. NMR (CDCl3) δ: 1.58 (9H, s), 3.56 (1H, t, J=9.8 Hz), 3.88-3.97 (2H, m), 3.93 (3H, s), 4.09 (1H, m), 4.19 (1H, m), 5.22 (2H, s), 7.08 (1H, d, J=2.0 Hz), 7.39-7.50 (5H, m), 7.81 (1H, brs), 9.03 (1H, s). [α]D25 =-29.3° (c 0.18, methanol).

Workup

  1. customThe solvent was evaporated from the reaction mixture
  2. customto give a residue, which
  3. customwas then purified by silica gel column chromatography
  4. customfollowed by crystallization from hexane

Sources & evidence

ORD record
ord-e5ba70902e094295bb8d739a5c79b437
Source dataset
uspto-grants-2000_05
Patent number
US06066742

Reaction notes

Loading…