Ammonium Chloride → HCID 86706763, compound

HRID 710050Notes

Reaction equation

HRID 710050 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][C:11]#[CH:12])=[CH:5][C:4]=1[O:13][CH3:14].[Li]CCCC.CON(C)[C:23]([C@@H:25]1[CH2:29][CH2:28][CH2:27][N:26]1[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:24].[NH4+].[Cl-]>C1COCC1>[CH3:14][O:13][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[O:9][CH2:10][C:11]#[C:12][C:23]([C@@H:25]1[CH2:29][CH2:28][CH2:27][N:26]1[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:24]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 6882981,1-Dimethylethyl (2S)-2-[(methoxymethylamino)carbonyl]-1-pyrrolidinecarboxylateHCID 11252509HCID 11252509, compoundHCID 178418339Butyllithium

Product 1

HCID 86706763HCID 86706763, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a THF (50 mL) solution of 1,2-dimethoxy-4-(prop-2-yn-yloxy)benzene (2.118 g), n-BuLi (4.0 mL, 2.64 N hexane solution) was added dropwise at −78° C. and the resulting mixture was stirred at the same temperature for 30 minutes; the reaction mixture was then added dropwise to a solution of (S)-t-butyl 2-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate (2.578 g) in THF (100 mL) at −78° C. and, after stirring at the same temperature for an hour, temperature was raised to room temperature over an hour. The reaction mixture was added to a saturated aqueous solution of NH4Cl (300 mL) to separate the organic layer, which was washed with a saturated aqueous solution of NH4Cl (100 mL), dried (Na2SO4), filtered and concentrated to give a crude product, which was further purified by neutral silica gel chromatography (AcOEt/hexane) to give the titled compound (2.479 g, pale brown oil.)

Workup

  1. stirringafter stirring at the same temperature for an hour
  2. customto separate the organic layer, which
  3. washwas washed with a saturated aqueous solution of NH4Cl (100 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude product, which
  8. customwas further purified by neutral silica gel chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-01c9b3539473442190909446c95c53fc
Source dataset
uspto-grants-2015_11
Patent number
US09181229B2

Reaction notes

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