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

HRID 1033295

반응식

HRID 1033295 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-867ba56c955f4cf0a007787c16965ca9
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05310743

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