Triethylamine → Tert-butyl 4-(1,1-dioxidothietan-3-yl)piperazine-1-carboxylate

HRID 1241427Notes

Reaction equation

HRID 1241427 reaction equation
Cl[CH:2]1[CH2:5][S:4](=[O:7])(=[O:6])[CH2:3]1.C(N(CC)CC)C.NC1N=CN=C([N:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]2)C=1>C(O)CCC>[O:6]=[S:4]1(=[O:7])[CH2:5][CH:2]([N:22]2[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:26][CH2:27]2)[CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2656363-Chloro-1lambda6-thietane-1,1-dioneHCID 21934614tert-Butyl 4-(6-aminopyrimidin-4-yl)piperazine-1-carboxylate

Product 1

HCID 21060000Tert-butyl 4-(1,1-dioxidothietan-3-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
150 °C

Procedure

3-Chlorothietane 1,1-dioxide 50-1 (0.50 g, 3.56 mmol) was dissolved in n-butanol (4 mL) then triethylamine (1.08 g, 10.67 mmol) was added followed by tert-butyl piperazine-1-carboxylate 12-1 (0.66 g, 3.56 mmol). This was then stirred at 150° C. for 5 hours. Upon cooling the solid was filtered off, washed with n-butanol, ethyl ether and then purified on a silica column to afford 50-2. 1H-NMR (CDCl3): 4.10(complex, 4H); 3.46(t, 4H); 3.19(m, 1H); 2.36(t, 4H); 1.46(s, 9H).

Workup

  1. temperatureUpon cooling the solid
  2. filtrationwas filtered off
  3. washwashed with n-butanol, ethyl ether
  4. custompurified on a silica column
  5. customto afford 50-2

Sources & evidence

ORD record
ord-f82d0040d320477bad82445d9a6cd128
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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