o-Xylyl bromide → HCID 54269290, compound

HRID 443234Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:23])[CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:34][C:35]1[CH:42]=[CH:41][CH:40]=[CH:39][C:36]=1[CH2:37]Br>C1COCC1>[CH2:1]([O:8][C:9](=[O:23])[C:10]1([CH2:34][C:35]2[CH:42]=[CH:41][CH:40]=[CH:39][C:36]=2[CH3:37])[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:14][CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of N-t-butoxycarbonyl isonipecotic acid benzyl ester (13.34 g, 41.8 mmol) in THF (100 ml) at -78° C. was added sodium bis-trimethysilylamide (59 ml of a 1.0M THF solution, 59 mmol) over 15 min. The resulting orange solution was stirred at -78° C. for 1 hr and then treated dropwise with 2-methyl benzyl bromide (6.80 ml, 50.7 mmol) and then allowed to warm slowly to room temperature over 16 hrs. The reaction was quenched with saturated aqueous NH4Cl, diluted with H2O, and extracted with EtOAc. The combined organic extracts were washed with brine, and concentrated in vacuo to an orange gum. Chromatography (SiO2, gradient elution, 20 to 30% EtOAc in hexanes) afforded the product as a white solid.

Workup

temperatureto warm slowly to room temperature over 16 hrs
customThe reaction was quenched with saturated aqueous NH4Cl
additiondiluted with H2O
extractionextracted with EtOAc
washThe combined organic extracts were washed with brine
concentrationconcentrated in vacuo to an orange gum
washChromatography (SiO2, gradient elution, 20 to 30% EtOAc in hexanes)

Sources & evidence

ORD record: ord-3f86b495e78d414e9d67fe7e77d71d30
Source dataset: uspto-grants-1999_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05891889

Reaction notes

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