N,N,N',N'-Tetramethylethylenediamine → HCID 68973628, compound

HRID 1726128Notes

Reaction equation

HRID 1726128 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Li]C.[Li]CCCC.CN(CCN(C)C)C.[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][CH:38]([CH:41]=[O:42])[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29]>C1COCC1>[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][CH:38]([CH:41]([OH:42])[C:2]2[CH:7]=[CH:6][C:5]([S:8](=[O:10])(=[O:9])[NH:11][CH3:12])=[CH:4][CH:3]=2)[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29]

Participants

7

Reactant 5

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 1012154-bromo-N-methylbenzene-1-sulfonamideHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 178418339ButyllithiumHCID 178418348HCID 178418348, compound

Product 1

HCID 68973628HCID 68973628, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 4-bromo-N-methyl-benzenesulfonamide (Marvel; Smith, J. Am. Chem. Soc., 45, 1923, 2697) (1.00 g, 4.00 mmol) in THF (35 mL) at −78° C. was added MeLi (4.00 mmol) and the solution was stirred at −78° C. for 15 minutes. n-BuLi (1.95M in hexanes, 2.05 mL, 4.00 mmol) was then added. After the solution was stirred at −78° C. for 45 minutes, TMEDA (1.20 mL, 8.00 mmol) was added followed by a solution of 4-formyl-piperidine-1-carboxylic acid tert-butyl ester (4.76 g, 22.30 mmol) in THF (5 mL), and the mixture was stirred at −78° C. for 1 hour. Work-up and purification gave 4-[hydroxy-(4-methylsulfamoyl-phenyl)-methyl]-piperidine-1-carboxylic acid tert-butyl ester (622 mg, 41%) as a white foam.

Workup

  1. stirringAfter the solution was stirred at −78° C. for 45 minutes
  2. stirringthe mixture was stirred at −78° C. for 1 hour
  3. custompurification

Sources & evidence

ORD record
ord-5b829721853d451db835824e1311c700
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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