Triethylamine → Methyl 2-[2-[(1-methylethyl)thio]-5-nitrophenyl]-3-pyrrolidinecarboxylate

HRID 1438113Notes

Reaction equation

HRID 1438113 reaction equation
[CH:1]([S:4][C:5]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:6]=1/[CH:7]=[N:8]/[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])([CH3:3])[CH3:2].C(N(CC)CC)C>ClCCl.[Cl-].[Ti+4].[Cl-].[Cl-].[Cl-]>[CH:1]([S:4][C:5]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:6]=1[CH:7]1[CH:11]([C:12]([O:14][CH3:15])=[O:13])[CH2:10][CH2:9][NH:8]1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 178500505HCID 178500505, compound

Product 1

HCID 57942701Methyl 2-[2-[(1-methylethyl)thio]-5-nitrophenyl]-3-pyrrolidinecarboxylateYield 79.8%

Reagents, catalysts & solvents 2

HCID 160960Diamminetetrachlorotitanate(IV)CatalystHCID 6344DichloromethaneSolvent

Procedure

To 20B (12.0 g, 28.2 mmol) and triethylamine (7.86 mL, 56.4 mmol) in dichloromethane at −10° C. was added titanium chloride (113 mL, 1 M in dichloromethane) dropwise under argon. The reaction was stirred at rt for 4 h and then quenched with saturated potassium carbonate. The mixture was filtered through celite and the aqueous layer was extracted with dichloromethane (2×). The organic extracts were combined, washed with brine and dried over sodium sulfate. The solvent was evaporated to give 7.3 g of crude pyrrolidine 20C.

Workup

  1. customquenched with saturated potassium carbonate
  2. filtrationThe mixture was filtered through celite
  3. extractionthe aqueous layer was extracted with dichloromethane (2×)
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-7b2b8f39db8940808a5ff06ebe7b7972
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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