Chlorotrimethylsilane → 1-(Trimethylsilyl)pyrrolidine

HRID 1192996Notes

Reaction equation

HRID 1192996 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[Si:7]([CH3:10])([CH3:9])[CH3:8]>C(OCC)C>[CH3:8][Si:7]([CH3:10])([CH3:9])[N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 31268Pyrrolidine

Product 1

HCID 847911-(Trimethylsilyl)pyrrolidineYield 73%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Step 1—To an ice-cold solution of pyrrolidine (167 ml, 2.00 mol) in diethyl ether (500 ml) was added a solution of chlorotrimethylsilane (127 ml, 1.00 mol) in diethyl ether (100 ml) over 1 hour. The solid was removed by filtration and washed with diethyl ether (100 ml). The filtrates were concentrated in vacuo then distilled at atmospheric pressure to give N-trimethylsilylpyrrolidine (104 g, 73%) as a colorless liquid: b.p. 139-140° C.; 1H NMR (CDCl3) 0.09 (s, 9H), 1.74 (m, 4H), 2.91 (m, 4H); 13C NMR (CDCl3) 3.50, 28.26, 48.33

Workup

  1. customThe solid was removed by filtration
  2. washwashed with diethyl ether (100 ml)
  3. concentrationThe filtrates were concentrated in vacuo
  4. distillationthen distilled at atmospheric pressure

Sources & evidence

ORD record
ord-30676b2be11144e9985edcc3f01a3a9b
Source dataset
uspto-grants-2014_03
Patent number
US08680332B2

Reaction notes

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