Acetic Acid → HCID 57293869, compound

HRID 1033307Notes

Reaction equation

HRID 1033307 reaction equation
[C:1]1([CH2:7][CH:8]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10]([C@@H:17]1[CH2:22][C@@H:21]([N:23]([CH2:30][C:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:34]=[CH:33][CH:32]=2)[C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])[CH2:20][CH2:19][NH:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])(=O)C.[Na+].C([BH3-])#N.[Na+].C(O)(=O)C>C(O)C>[CH2:10]([C@@H:17]1[CH2:22][C@@H:21]([N:23]([CH2:30][C:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:34]=[CH:33][CH:32]=2)[C:24](=[O:29])[C:25]([F:27])([F:28])[F:26])[CH2:20][CH2:19][N:18]1[CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 998PhenylacetaldehydeHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 57202094(2R*,4S*)-2-Benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

Product 1

HCID 57293869HCID 57293869, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

209 μl (0.936 mmol) of phenylacetaldehyde are added dropwise over the course of 10 minutes to a solution of 100 mg (0.233 mmol) of (2R*,4S*)-2-benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine, 58 mg (0.702 mmol) of sodium acetate, 44 mg (0.702 mmol) of sodium cyanoborohydride and 67 μl (1.17 mmol) of acetic acid in 2 ml of ethanol at room temperature. The reaction mixture is left to stir at room temperature for 16 hours. The residue after evaporation in a rotary evaporator is taken up in ethyl acetate, and the organic phase is washed with water and with brine, dried over magnesium sulfate and evaporated to dryness. The yellow oil is chromatographed on silica gel with methylene chloride/methanol/conc. ammonia (2000:50:1). The title compound is obtained as oil. TLC: methylene chloride/methanol/conc. ammonia (2000:50:1) Rf =0.33, FD-MS: M+ =531.

Workup

  1. waitThe reaction mixture is left
  2. customThe residue after evaporation
  3. customin a rotary evaporator
  4. washthe organic phase is washed with water and with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness
  7. customThe yellow oil is chromatographed on silica gel with methylene chloride/methanol/conc

Sources & evidence

ORD record
ord-d20d4cfc97a84e9aabbaf69b07c52259
Source dataset
uspto-grants-1994_05
Patent number
US05310743

Reaction notes

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