(+/-)-3-(1-methyl-2-pyrrolidinyl)-2-pyridyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside → (R)-(+)-3-(1-methyl-2-pyrrolidinyl)-2-pyridyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside

HRID 37452Notes

Reaction equation

HRID 37452 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:23]([O:24][C:25](=[O:27])[CH3:26])[C@H:22]([O:28][C:29](=[O:31])[CH3:30])[C@@H:21]([CH2:32][O:33][C:34](=[O:36])[CH3:35])[O:20][C@H:6]1[O:7][C:8]1[C:13]([CH:14]2[CH2:18][CH2:17][CH2:16][N:15]2[CH3:19])=[CH:12][CH:11]=[CH:10][N:9]=1)(=[O:3])[CH3:2]>C(OCC)(=O)C>[C:1]([O:4][C@@H:5]1[C@@H:23]([O:24][C:25](=[O:27])[CH3:26])[C@H:22]([O:28][C:29](=[O:31])[CH3:30])[C@@H:21]([CH2:32][O:33][C:34](=[O:36])[CH3:35])[O:20][C@H:6]1[O:7][C:8]1[C:13]([C@@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[CH3:19])=[CH:12][CH:11]=[CH:10][N:9]=1)(=[O:3])[CH3:2].[C:1]([O:4][C@@H:5]1[C@@H:23]([O:24][C:25](=[O:27])[CH3:26])[C@H:22]([O:28][C:29](=[O:31])[CH3:30])[C@@H:21]([CH2:32][O:33][C:34](=[O:36])[CH3:35])[O:20][C@H:6]1[O:7][C:8]1[C:13]([C@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[CH3:19])=[CH:12][CH:11]=[CH:10][N:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 15293694(+/-)-3-(1-methyl-2-pyrrolidinyl)-2-pyridyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside

Product 2

HCID 11027593(R)-(+)-3-(1-methyl-2-pyrrolidinyl)-2-pyridyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosideHCID 11081744(S)-(-)-3-(1-methyl-2-pyrrolidinyl)-2-pyridyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The diastereomer mixture (5a) was resolved by means of silica gel column chromatography using ethyl acetate as an eluent. As a result, (S)-(-)-3-(1-methyl-2-pyrrolidinyl)-2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (6a) and (R)-(+)-3-(1-methyl-2-pyrrolidinyl)-2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (7a) were obtained in white-solid form and in yields of 1.8 g and 1.7 g, respectively. Further, (S)-(-)-3-(1-methyl-2-pyrrolidinyl)-2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (6a) and (R)-(+)-3-(1-methyl-2-pyrrolidinyl)-2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (7a) were each recrystallized from ethyl acetate-hexane. As a result, highly purified (S)-(-)-3-(1-methyl-2-pyrrolidinyl)-2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (6a) and (R)-(+)-3-(1-methyl-2-pyrrolidinyl)-2-pyridyl 2,3,4,6tetra-O-acetyl-β-D-glucopyranoside (7a) were obtained in yields of 1.7 g (30%) and 1.6 g (28%), respectively.

Sources & evidence

ORD record
ord-a4e0219ba7d44a3aa5a8ad8b1015258b
Source dataset
uspto-grants-1995_05
Patent number
US05420286

Reaction notes

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