N-Methyldiethanolamine → HCID 85807772, compound

HRID 1369597Notes

Reaction equation

HRID 1369597 reaction equation
[C:1]1([S:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][N:16]([CH2:20][CH2:21]O)[CH2:17][CH2:18]O.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>C1COCC1>[CH3:15][N:16]1[CH2:20][CH2:21][C:10]([S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:9])=[O:8])([C:11]([O:13][CH3:14])=[O:12])[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 7767N-MethyldiethanolamineHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 555619Methyl phenylsulfonyl acetate

Product 1

HCID 85807772HCID 85807772, compoundYield 16.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

2-(Phenylsulfonyl)acetic acid, methyl ester (205 mg, 0.95 mmol) was dissolved in THF (20 ml), then treated with N-methyl-diethanolamine (111 μl, 0.97 mmol), 1,1′-(azodicarbonyl)-dipiperidine (483 mg, 1.91 mmol) then tributylphosphine (197 μl, 1.91 mmol). After 10 minutes the mixture was warmed to 40° C. After stirring for 3 hours the solvents were removed and the residue purified by flash column chromatography on silica gel eluted with 25-75% ethyl acetate in hexanes to give N-(N-methyl-4-(phenylsulfonyl)-isonipecotic acid, methyl ester (47 mg).

Workup

  1. customwere removed
  2. customthe residue purified by flash column chromatography on silica gel
  3. washeluted with 25-75% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-90e301443a3a435ba6fc5be61e3239ae
Source dataset
uspto-grants-2003_06
Patent number
US06579889B2

Reaction notes

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