Methyl 4-nitrobutyrate → 8-Benzyloxy-5-hydroxy-4-nitrooctanoic acid methyl ester

HRID 2197655

Reaction equation

HRID 2197655 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:14][O:15][C:16](=[O:23])[CH2:17][CH2:18][CH2:19][N+:20]([O-:22])=[O:21].C1C[C@H]2N(C[C@H]3[C@@H]4CCCCN4C[C@@H]2C3)CC1>CCOC(C)=O>[CH3:14][O:15][C:16](=[O:23])[CH2:17][CH2:18][CH:19]([N+:20]([O-:22])=[O:21])[CH:12]([OH:13])[CH2:11][CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25604Methyl 4-nitrobutyrateHCID 2315594-BenzyloxybutanalHCID 644020Sparteine

Product 1

HCID 593362278-Benzyloxy-5-hydroxy-4-nitrooctanoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-benzyloxybutanal (1.463 g, 8.2 mmol), methyl-4-nitrobutyrate (1.29 g, 8.8 mmol) and (−)-sparteine (206 mg, 0.88 mmol) are combined and stirred at RT for 6 hours. EtOAc (5 mL) is added, and the solution is filtered through silica. The solvent is removed in vacuo to yield a pale yellow oil.

Workup

  1. filtrationthe solution is filtered through silica
  2. customThe solvent is removed in vacuo
  3. customto yield a pale yellow oil

Sources & evidence

ORD record
ord-9d4ca1a4aa13472e813b368569984535
Source dataset
uspto-grants-2012_12
Patent number
US08338620B2

Linked notes

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