Carbon tetrabromide → 2-Trimethylsilanylethyl 4-bromomethyl-piperidine-1-carboxylate

HRID 1743266Notes

Reaction equation

HRID 1743266 reaction equation
O[CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])=[O:10])[CH2:5][CH2:4]1.[Br:18]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:18][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])=[O:10])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 113689482-(Trimethylsilyl)ethyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 222383942-Trimethylsilanylethyl 4-bromomethyl-piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

19.9 g of 2-trimethylsilanylethyl 4-hydroxymethylpiperidine-1-carboxylate were dissolved in 600 ml of THF. After cooling to 0° C., 50.7 g of tetrabromomethane were added. Then 42.1 g of triphenylphosphine were added in 4 portions at intervals each of 20 min. The mixture was allowed to reach room temperature and was stirred for 14 h. The solvent was then removed in vacuo, and the residue was chromatographed on silica gel.

Workup

  1. customto reach room temperature
  2. customThe solvent was then removed in vacuo
  3. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-48b3313e1087426b80b264767c1bb6bb
Source dataset
uspto-grants-2006_03
Patent number
US07008957B2

Reaction notes

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