4-Chlorobenzaldehyde → 1-(4-Chlorobenzyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-(cyclopropyl)pyrrolidine

HRID 279218Notes

Reaction equation

HRID 279218 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH:15]3[CH:19]([CH:20]4[CH2:22][CH2:21]4)[CH2:18][NH:17][CH2:16]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[K+].[K+]>ClC(Cl)C.O>[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][N:17]2[CH2:18][CH:19]([CH:20]3[CH2:21][CH2:22]3)[CH:15]([CH2:14][N:11]3[CH2:12][CH2:13][CH:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[CH2:9][CH2:10]3)[CH2:16]2)=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 77264-ChlorobenzaldehydeHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 226244713-(RS)-(4-(4-Fluorophenyl)piperidinylmethyl)-4-(SR)-(cyclopropyl)pyrrolidine

Product 1

HCID 99542321-(4-Chlorobenzyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-(cyclopropyl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 0.02 g (0.07 mmol) of 3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-(cyclopropyl)pyrrolidine and 0.018 g (0.1 mmol) of 4-chlorobenzaldehyde (Aldrich) in 5 mL of dichloroethane at rt was added 0.063 g (0.3 mmol) of sodium triacetoxyborohydride and the reaction mixture was stirred for 3 h. To the reaction mixture was added a few drops of H2O and 5 mL of sat'd K2CO3 solution. The reaction mixture was extracted with ethyl acetate. The organic fractions were dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by chomatography (silica, acetone: hexanes, 15%) to give the title compound.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. dry with materialThe organic fractions were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chomatography (silica, acetone: hexanes, 15%)

Sources & evidence

ORD record
ord-75d7930c2b554f22b560cb917ded3a35
Source dataset
uspto-grants-2002_03
Patent number
US06362201B1

Reaction notes

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