Ammonium Chloride → HCID 57145839, compound

HRID 1078729Notes

Reaction equation

HRID 1078729 reaction equation
[CH2:1]([N:8]([CH3:12])[C:9](=[O:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N-]C(C)C)(C)C.[Li+].C(OC([N:28]1[CH2:34][C@H:33]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[CH2:32][C@H:29]1[CH:30]=[O:31])=O)(C)(C)C.[Cl-].[NH4+]>O1CCCC1.O.C(OCC)(=O)C>[CH2:1]([N:8]([CH3:12])[C:9]([CH2:10][CH:30]([C@@H:29]1[CH2:32][C@@H:33]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:37])[CH3:38])[CH2:34][NH:28]1)[OH:31])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 457821029823-47-0HCID 10969557tert-Butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-formylpyrrolidine-1-carboxylate

Product 1

HCID 57145839HCID 57145839, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent4×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

Under a nitrogen atmosphere, a solution of N-benzyl-N-methylacetamide (280 mg, 1.67 mmol) in tetrahydrofuran (1 ml) was dropwise added at -78° C. to a solution comprising a 2.0M lithium diisopropylamide--tetrahydrofuran solution (835 μl, 1.67 mmol) and tetrahydrofuran (15 ml). The mixture was stirred at -78° C. for 10 minutes, and then a solution of (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxyprolinal (500 mg, 1.52 mmol) in tetrahydrofuran (1 ml) was dropwise added thereto. The reaction mixture was stirred at the same temperature for 10 minutes. Saturated aqueous ammonium chloride was added to the reaction mixture, and then the reaction mixture was poured into a mixture of ethyl acetate--water. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated in vacuo. The obtained oily residue was subjected to silica gel column chromatography (heptane-ethyl acetate=2:1) to give the title compound (549 mg, yield: 73.6%).

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for 10 minutes
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c8977649666a4e01a1abdd6a25182300
Source dataset
uspto-grants-1996_08
Patent number
US05550121

Reaction notes

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