Pyridine → HCID 70117622, compound

HRID 1282004Notes

Reaction equation

HRID 1282004 reaction equation
[Cl:1][C:2]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:3]=1[CH2:4][N:5]1[CH2:9][C@H:8]([C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[C@@H:7]([CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][O:23][CH2:24][CH2:25][CH2:26][OH:27])[CH2:18][CH2:17]2)[CH2:6]1.[C:33](OC(=O)C)(=[O:35])[CH3:34].N1C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:1][C:2]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:3]=1[CH2:4][N:5]1[CH2:9][C@H:8]([C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[C@@H:7]([CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][O:23][CH2:24][CH2:25][CH2:26][O:27][C:33](=[O:35])[CH3:34])[CH2:18][CH2:17]2)[CH2:6]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 10117643HCID 10117643, compound

Product 1

HCID 70117622HCID 70117622, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.02 g (0.04 mmol) of 1-(2,4-dichlorobenzyl)-3-(S)-(4-(3-hydroxypropyloxymethyl)piperidinylmethyl)-4-(S)-(3-thienyl)pyrrolidine (Example 17), 0.25 mL (0.12 mmol) of acetic anhydride, 0.25 mL (0.3 mmol) of pyridine and a catalytic amount of DMAP in 0.5 mL of CH2Cl2 was stirred at rt for 2 h. TO the reaction mixture was added 10 mL of sat'd Na2CO3 solution and it was extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ethyl acetate, 1:1) to give the title compound. Mass Spectrum (ESI) m/e=539 (M+1 35Cl, 35Cl), 541 (M+1 35Cl, 37Cl), and 543 (M+1 37Cl, 37Cl).

Workup

  1. extractionwas extracted with CH2Cl2
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chromatography (silica, hexanes:ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-bf015af8e8f049b59d21e4b8cc6ce050
Source dataset
uspto-grants-2002_09
Patent number
US06455548B2

Reaction notes

Loading…