Triethylamine → tert-Butyl (2R)-4-[(6-bromo-1-oxo-1,2-dihydroisoquinolin-4-yl)sulfonyl]-2-(hydroxymethyl)piperazine-1-carboxylate

HRID 906449Notes

Reaction equation

HRID 906449 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][NH:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C(N(CC)CC)C.[Br:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[C:30](=[O:34])[NH:29][CH:28]=[C:27]2[S:35](Cl)(=[O:37])=[O:36]>C1COCC1>[Br:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[C:30](=[O:34])[NH:29][CH:28]=[C:27]2[S:35]([N:7]1[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@@H:3]([CH2:2][OH:1])[CH2:8]1)(=[O:37])=[O:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24820219(R)-2-Hydroxymethyl-piperazine-1-carboxylic acid tert-butyl esterHCID 574399001220229-87-7

Product 1

HCID 67392085tert-Butyl (2R)-4-[(6-bromo-1-oxo-1,2-dihydroisoquinolin-4-yl)sulfonyl]-2-(hydroxymethyl)piperazine-1-carboxylateYield 76.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl (2R)-2-(hydroxymethyl)piperazine-1-carboxylate (0.479 g) and triethylamine (0.618 mL) in THF (6 mL) was added dropwise a solution of 6-bromo-1-oxo-1,2-dihydroisoquinoline-4-sulfonyl chloride (Example 46a, 0.715 g) in THF (10 mL). The reaction was stirred at room temperature for 20 min. The resulting solution was concentrated under reduced pressure before adding water and extracting into ethyl acetate. The combined organics were dried (MgSO4), filtered and evaporated under reduced pressure. Trituration with ethyl acetate gave the subtitle compound (0.855 g).

Workup

  1. concentrationThe resulting solution was concentrated under reduced pressure
  2. additionbefore adding water
  3. extractionextracting into ethyl acetate
  4. dry with materialThe combined organics were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e8b7d749de1247138d8596060c97ce7e
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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