Acetone → (2R*,4S*)-2-Benzyl-1-(2-naphthoyl)-N-(4-quinolylmethyl)-4-piperidinamine

HRID 264607Notes

Reaction equation

HRID 264607 reaction equation
[BH4-].[Na+].[CH2:3]([C@@H:10]1[CH2:15][C@@H:14]([N:16]([CH2:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=[CH:26][CH:25]=2)C(=O)C(F)(F)F)[CH2:13][CH2:12][N:11]1[C:34]([C:36]1[CH:45]=[CH:44][C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=1)=[O:35])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CC(C)=O>CO>[CH2:3]([C@@H:10]1[CH2:15][C@@H:14]([NH:16][CH2:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=[CH:26][CH:25]=2)[CH2:13][CH2:12][N:11]1[C:34]([C:36]1[CH:45]=[CH:44][C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=1)=[O:35])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 57190025(2R*,4S*)-2-benzyl-1-(2-naphthoyl)-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

Product 1

HCID 9957036(2R*,4S*)-2-Benzyl-1-(2-naphthoyl)-N-(4-quinolylmethyl)-4-piperidinamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

28 mg (0.73 mmol) of sodium borohydride are added in three portions over the course of 20 minutes to a solution of 106 mg (0.182 mmol) of (2R*,4S*)-2-benzyl-1-(2-naphthoyl)-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine in 1.5 ml of methanol at 0°, and the mixture is subsequently stirred at 0° for 3 hours. 0.06 ml (0.81 mmol) of acetone is then added to the reaction mixture, and the stirring is completed for 10 minutes. The methanol is removed in a rotary evaporator, and the solid white residue is partitioned between ethyl acetate and water. The organic phases are washed with brine, dried over magnesium sulfate and evaporated to dryness. The resulting white foam is chromatographed with methylene chloride/methanol/conc. ammonia (1500:50:1) on silica gel. The title compound of the formula ##STR28## as white foam is obtained as white foam. TLC: methylene chloride/methanol/conc. ammonia (700:50:1) Rf =0.34, FD-MS: M+ =485.

Workup

  1. waitthe stirring is completed for 10 minutes
  2. customThe methanol is removed in a rotary evaporator
  3. customthe solid white residue is partitioned between ethyl acetate and water
  4. washThe organic phases are washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness
  7. customThe resulting white foam is chromatographed with methylene chloride/methanol/conc

Sources & evidence

ORD record
ord-9fc372e762fc414a8d77c1339cc2afcb
Source dataset
uspto-grants-1997_07
Patent number
US05646144

Reaction notes

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