Benzaldehyde → HCID 67374843, compound

HRID 1677087Notes

Reaction equation

HRID 1677087 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([O:11][C:12]([C@H:14]1[CH2:18][CH2:17][C@@H:16]([C:19]2[CH:24]=[C:23]([F:25])[C:22]([F:26])=[C:21]([F:27])[CH:20]=2)[NH:15]1)=[O:13])[CH3:10].[Na].[Cl-].[NH4+]>C(OCC)(=O)C.O1CCCC1.CO.C(O)(=O)C>[CH2:9]([O:11][C:12]([C@H:14]1[CH2:18][CH2:17][C@@H:16]([C:19]2[CH:24]=[C:23]([F:25])[C:22]([F:26])=[C:21]([F:27])[CH:20]=2)[N:15]1[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:13])[CH3:10]

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 67373176ethyl (2R,5S)-5-(3,4,5-trifluorophenyl)pyrrolidine-2-carboxylate

Product 1

HCID 67374843HCID 67374843, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Benzaldehyde (2.46 mL) and acetic acid (3 mL) were added to a tetrahydrofuran/methanol (80 mL, 4/1) solution of (2R,5S)-5-(3,4,5-trifluorophenyl)pyrrolidine-2-carboxylic acid ethyl ester (3.42 g) obtained in Example 14. Stirring was continued for 10 minutes at room temperature. Sodium triacetoxybrohydride (5.15 g) was added to the reaction solution, and stirring was continued for 3.5 days. Ammonium chloride aqueous solution and ethyl acetate were added, and the organic layer was partitioned. The organic layer was washed with brine, and the resultant was dried with magnesium sulfate. The solvent was removed under a vacuum, and the residue was purified by silica gel column chromatography (heptane/ethyl acetate), and the title compound (3.43 g) was obtained. The physical property values are as follows.

Workup

  1. stirringstirring
  2. waitwas continued for 3.5 days
  3. customthe organic layer was partitioned
  4. washThe organic layer was washed with brine
  5. dry with materialthe resultant was dried with magnesium sulfate
  6. customThe solvent was removed under a vacuum
  7. customthe residue was purified by silica gel column chromatography (heptane/ethyl acetate)

Sources & evidence

ORD record
ord-2458f8ba805e46c588fcec0880bc6e52
Source dataset
uspto-grants-2011_08
Patent number
US08008293B2

Reaction notes

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