Imidazole → 3-((trans-4-hydroxy-2-(S)-pyrrolidinyl)methoxy)pyridine dihydrochloride

HRID 617342Notes

Reaction equation

C([N:11]1[CH2:19][CH2:18][CH2:17][C@H:12]1[C:13]([O:15][CH3:16])=O)(OCC1C=CC=CC=1)=O.[NH:20]1[CH:24]=CN=C1.[Si]([Cl:32])([C:28]([CH3:31])(C)[CH3:29])(C)C.CN(C=[O:37])C>>[ClH:32].[ClH:32].[OH:37][C@H:18]1[CH2:19][NH:11][C@H:12]([CH2:13][O:15][C:16]2[CH:24]=[N:20][CH:29]=[CH:28][CH:31]=2)[CH2:17]1

Participants

Reactant 4

HCID 795Imidazole

HCID 6228Dimethylformamide

HCID 28928tert-Butyldimethylsilyl chloride

HCID 688168(S)-1-Benzyl 2-methyl pyrrolidine-1,2-dicarboxylate

Product 1

HCID 675868713-((trans-4-hydroxy-2-(S)-pyrrolidinyl)methoxy)pyridine dihydrochloride

Conditions

Temperature: -23 °C

Procedure

A 7.5 g sample of the compound from step 72a was dissolved in 140 mL of DMF and 2.2 g of imidazole was added. The solution was cooled to -23° C., and 4.84 g of t-butyldimethylsilyl chloride was added and stirred for 1 hour. The volatiles were removed under vacuum, and the residue was purified on a silica gel column, eluting with 1:2 ethyl acetate:hexane to give 8.05 g of the title compound.

Workup

customThe volatiles were removed under vacuum
customthe residue was purified on a silica gel column
washeluting with 1:2 ethyl acetate

Sources & evidence

ORD record: ord-4b592efb675745b9a995ff7f508638b7
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05948793

Reaction notes

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