Diisopropylethylamine → HCID 57979768, compound

HRID 1868028Notes

Reaction equation

HRID 1868028 reaction equation
[CH3:1][C@H:2]1[NH:7][C@H:6]([CH3:8])[CH2:5][N:4]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:3]1.C(N(C(C)C)CC)(C)C.[C:28]([C:32]1[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1)([CH3:31])([CH3:30])[CH3:29]>ClCCl>[C:28]([C:32]1[CH:37]=[CH:36][C:35]([S:38]([N:7]2[C@@H:2]([CH3:1])[CH2:3][N:4]([C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:10])[CH2:5][C@@H:6]2[CH3:8])(=[O:40])=[O:39])=[CH:34][CH:33]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 57979764HCID 57979764, compound

Product 1

HCID 57979768HCID 57979768, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (3R,5R)-benzyl 3,5-dimethylpiperazine-1-carboxylate (500 mg, 2.02 mmol) in anhydrous dichloromethane (8 mL) was added diisopropylethylamine (1.4 mL, (8.08 mmol) followed by 4-tert-butylbenzene-1-sulfonyl chloride (940 mg, 4.04 mmol). The reaction mixture was stirred for 68 hours. Reaction was complete as determined by TLC. After solvent evaporation the crude product was purified by flash column chromatography to afford benzyl (3S,5S)-4-[(4-tert-butylphenyl)sulfonyl]-3,5-dimethylpiperazine-1-carboxylate in 42% yield (377 mg) as light yellow oil.

Workup

  1. customReaction
  2. customAfter solvent evaporation the crude product
  3. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-b36ed2d8bb0e4b1eba619f1dcd8dfadd
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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