Lithium diisopropylamide → 3-(2,4-Dichloro-benzyl)-1-(cis-7-methyl-1,4-dioxa-spiro[4.5]dec-8-yl)-pyrrolidin-2-one

HRID 2235249Notes

Reaction equation

HRID 2235249 reaction equation
[CH3:1][C@H:2]1[C@@H:11]([N:12]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])[CH2:10][CH2:9][C:4]2([O:8][CH2:7][CH2:6][O:5]2)[CH2:3]1.[Li+].CC([N-]C(C)C)C.Br[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=1[Cl:35]>>[Cl:35][C:29]1[CH:30]=[C:31]([Cl:34])[CH:32]=[CH:33][C:28]=1[CH2:27][CH:14]1[CH2:15][CH2:16][N:12]([C@H:11]2[CH2:10][CH2:9][C:4]3([O:5][CH2:6][CH2:7][O:8]3)[CH2:3][C@H:2]2[CH3:1])[C:13]1=[O:17]

Participants

4

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 109883732,4-Dichlorobenzyl bromideHCID 684686771-(cis-7-Methyl-1,4-dioxa-spiro[4.5]dec-8-yl)-pyrrolidin-2-one

Product 1

HCID 684723163-(2,4-Dichloro-benzyl)-1-(cis-7-methyl-1,4-dioxa-spiro[4.5]dec-8-yl)-pyrrolidin-2-oneYield 56.5%

Procedure

Using the procedure to synthesize Example 1 and using reagent 1-(cis-7-methyl-1,4-dioxa-spiro[4.5]dec-8-yl)-pyrrolidin-2-one (Preparation 45) (2.49 g, 10.4 mmol), LDA (1.5M, 8.3 mL, 12.5 mmol) and 1-(bromomethyl)-2,4-dichlorobenzene (4.07 g, 20.8 mmol) yields 2.34 g (56%) of 3-(2,4-dichloro-benzyl)-1-(cis-7-methyl-1,4-dioxa-spiro[4.5]dec-8-yl)-pyrrolidin-2-one as a white solid.

Workup

  1. customto synthesize Example 1

Sources & evidence

ORD record
ord-5c85eeebd0e94cb9ac3269bf7bf8d0d2
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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