Triethylamine → 1-(4,6-Di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-carbonyl)pyrrolidine

HRID 367304Notes

Reaction equation

HRID 367304 reaction equation
[C:1]([C:5]1[C:10]2[CH2:11][C:12]([CH3:17])([C:14](O)=[O:15])[O:13][C:9]=2[CH:8]=[C:7]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=1[O:22][Si:23]([CH3:26])([CH3:25])[CH3:24])([CH3:4])([CH3:3])[CH3:2].[CH2:27]([N:29](CC)[CH2:30][CH3:31])[CH3:28].N1CCCC1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>ClCCl>[C:1]([C:5]1[C:10]2[CH2:11][C:12]([CH3:17])([C:14]([N:29]3[CH2:30][CH2:31][CH2:28][CH2:27]3)=[O:15])[O:13][C:9]=2[CH:8]=[C:7]([C:18]([CH3:20])([CH3:19])[CH3:21])[C:6]=1[O:22][Si:23]([CH3:25])([CH3:26])[CH3:24])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 232880354,6-Di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-carboxylic acid

Product 1

HCID 232880321-(4,6-Di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-carbonyl)pyrrolidineYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 3 ml of dichloromethane were dissolved 0.20 g of 4,6-di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-carboxylic acid, 0.20 ml of triethylamine and 0.06 ml of pyrrolidine at room temperature, and 0.35 g of benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate was added and the mixture was stirred for 4 hours. The mixture was extracted with water and diethyl ether, and the combined organic layers were washed with saturated brine and dried over anhydrous magnesium sulfate. After concentration, the residue was purified by silica gel column chromatography eluting with n-hexane containing 33% ethyl acetate to give 0.21 g of 1-(4,6-di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-carbonyl)pyrrolidine as a colorless solid (yield 92%).

Workup

  1. extractionThe mixture was extracted with water and diethyl ether
  2. washthe combined organic layers were washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationAfter concentration
  5. customthe residue was purified by silica gel column chromatography
  6. washeluting with n-hexane containing 33% ethyl acetate

Sources & evidence

ORD record
ord-d3602439b0db4917a2a1a62a6a21f456
Source dataset
uspto-grants-2000_10
Patent number
US06133279

Reaction notes

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