Pyrrolidine → HCID 86761070, compound

HRID 2245920Notes

Reaction equation

HRID 2245920 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:26][C@H:25]([CH2:27][O:28]C(=O)C)[C@@H:20]([O:21]C(=O)C)[C@H:15]([O:16]C(=O)C)[C@H:10]2[O:11]C(=O)C)[OH:9])=[CH:4][C:3]=1[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][C:40]2([CH2:45][O:46][CH3:47])[CH2:44][CH2:43][CH2:42][CH2:41]2)=[CH:35][CH:34]=1.N1CCCC1>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:26][C@H:25]([CH2:27][OH:28])[C@@H:20]([OH:21])[C@H:15]([OH:16])[C@H:10]2[OH:11])[OH:9])=[CH:4][C:3]=1[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][C:40]2([CH2:45][O:46][CH3:47])[CH2:41][CH2:42][CH2:43][CH2:44]2)=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 86611024HCID 86611024, compound

Product 1

HCID 86761070HCID 86761070, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-chloro-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-2-[4-(1-methoxymethyl-cyclopent-1-yloxy)-benzyl]-benzene (0.39 g) in tetrahydrofuran (3 mL) is added pyrrolidine (0.22 mL). The solution is stirred at ambient temperature for 16 h. After dilution with ethyl acetate, the resulting solution is washed with aqueous hydrochloric acid (1 mol/l), dried (Na2SO4) and the solvent is removed under reduced pressure. The residue is purified by HPLC on reversed phase (YMC C18; water/acetonitrile 95:5→2:98).

Workup

  1. washAfter dilution with ethyl acetate, the resulting solution is washed with aqueous hydrochloric acid (1 mol/l)
  2. dry with materialdried (Na2SO4)
  3. customthe solvent is removed under reduced pressure
  4. customThe residue is purified by HPLC on reversed phase (YMC C18; water/acetonitrile 95:5→2:98)

Sources & evidence

ORD record
ord-3beb2dee2f334a87a45e1993044dd06a
Source dataset
uspto-grants-2010_03
Patent number
US07683160B2

Reaction notes

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