Carbon tetrabromide → 1-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-(bromomethyl)spiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylate

HRID 1411310Notes

Reaction equation

HRID 1411310 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]2[C:11]3([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]3)[CH2:10][N:9]([C:23]([O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])=[O:24])[C:6]2=[CH:7][CH:8]=1.C(Br)(Br)(Br)[Br:33].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:33][CH2:2][C:3]1[CH:4]=[C:5]2[C:11]3([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]3)[CH2:10][N:9]([C:23]([O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])=[O:24])[C:6]2=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 904495331-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-(hydroxymethyl)spiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylate

Product 1

HCID 904495541-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-(bromomethyl)spiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylateYield 77.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-(Trimethylsilyl)ethyl) 1′-tert-butyl 5-(hydroxymethyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (441 mg, 0.98 mmol) was dissolved in methylene chloride (10 mL). Thereafter, carbon tetrabromide (359 mg, 1.08 mmol) and triphenylphosphine (310 mg, 1.18 mmol) were added to the above obtained solution under cooling on ice, and the thus obtained mixture was then stirred at the same temperature as above for 2.5 hours. Thereafter, the reaction solution was concentrated in vacuo, and the obtained residue was then purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl 5-(bromomethyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (390 mg, 77%) in the form of a colorless amorphous product.

Workup

  1. temperatureunder cooling on ice
  2. concentrationThereafter, the reaction solution was concentrated in vacuo
  3. customthe obtained residue was then purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-ed837e15572a40ab8d665eb9e5b76ee4
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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