Nitromethane → HCID 57230569, compound

HRID 2185494Notes

Reaction equation

HRID 2185494 reaction equation
CN(C)C(N(C)C)=N.[N+:9]([CH3:12])([O-:11])=[O:10].[C:13]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C@H:20]2[CH2:24][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:22]([CH:32]=[O:33])[CH2:21]2)[CH:14]=1>O1CCCC1>[N+:9]([CH2:12][CH:32]([C@@H:22]1[CH2:21][C@@H:20]([O:19][C:15]2[CH:14]=[C:13]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:18]=[CH:17][CH:16]=2)[CH2:24][N:23]1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[OH:33])([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 664601,1,3,3-TetramethylguanidineHCID 56985310HCID 56985310, compound

Product 1

HCID 57230569HCID 57230569, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1,3,3-Tetramethylguanidine (52 μL) and nitromethane (222 μl) were added to a solution of crude (2S,4R)-4-(3-biphenyloxy)-N-tert-butoxycarbonyl-2-pyrrolidinecarboxaldehyde (B, 754 mg) in tetrahydrofuran (15 mL). The mixture was stirred at room temperature for 3 hr and evaporated in vacuo. The residue was diluted with ethyl acetate and washed with brine. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo to give crude the titled compound (877 mg), which was used in the subsequent step.

Workup

  1. customevaporated in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-68d8066f82b74a459127b3d552b1ac05
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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