4-(Bromomethyl)benzonitrile → HCID 70090413, compound

HRID 2394084Notes

Reaction equation

HRID 2394084 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1.CCCCCC.C(OCC)(=O)C.[C:33]([NH:40][C@H:41]([C@H:49]1[O:53][C:52](=[O:54])[CH2:51][CH2:50]1)[CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34]>C1COCC1>[C:33]([NH:40][C@H:41]([C@H:49]1[O:53][C:52](=[O:54])[C@H:51]([CH2:12][C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)[CH2:50]1)[CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([O:35][C:36]([CH3:38])([CH3:39])[CH3:37])=[O:34]

Participants

6

Reactant 4

HCID 869964-(Bromomethyl)benzonitrileHCID 2733832Lithium HexamethyldisilazideHCID 10870461tert-butyl(1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamateHCID 21226206Ethyl acetate hexane

Product 1

HCID 70090413HCID 70090413, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In analogy with Example 1h), 1.5 g of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]dihydrofuran-2-(3H)-one, dissolved in 32 ml of THF, are deprotonated with 9.8 ml of a 1M solution of lithium bis(trimethylsilyl)amide in THF, and alkylated with 1.0 g of 4-bromomethylbenzonitrile (Fluka; Buchs/Switzerland) dissolved in 3 ml of THF. Column chromatography (SiO2, hexane/ethyl acetate 1:1) affords the pure title compound: TLC Rf (B)=0.33.

Sources & evidence

ORD record
ord-04ea3ce24bf44965a5e4561bb9a42565
Source dataset
uspto-grants-1998_09
Patent number
US05807891

Reaction notes

Loading…