1,5-Dibromopentane → HCID 19757899, compound

HRID 1587543Notes

Reaction equation

[H-].[Na+].[CH3:3][S:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:12][CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:7][CH:6]=1.[H][H].Br[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]Br>CN(C)C=O>[CH3:3][S:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:12][CH2:13][CH2:14][N:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][N:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:13][CH2:12][N:11]([C:8]2[CH:9]=[CH:10][C:5]([S:4][CH3:3])=[CH:6][CH:7]=2)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Suspend sodium hydride (48 mg, 2 mmol) in anhydrous dimethylformamide (2 mL), cool to 0° C. and place under a nitrogen atmosphere. Add, by dropwise addition, a solution 1-(4-methylthiophenyl)-1,5-bis(t-butyloxycarbonyl)-1,5-diazapentane (1.58 g, 4 mmol) in dimethylformamide (2 mL). Stir until evolution of hydrogen ceases. Add, by dropwise addition, a solution of 1,5-dibromopentane (460 mg, 2 mmol) in dimethylformamide (2 mL). Stir overnight at room temperature then carefully quench with saturated ammonium chloride. Extract into ethyl acetate, dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatogaphy to give the title compound.

Workup

additionAdd, by dropwise addition
additionAdd, by dropwise addition
customthen carefully quench with saturated ammonium chloride
extractionExtract into ethyl acetate
dry with materialdry (MgSO4)
customevaporate the solvent in vacuo
customPurify by silica gel chromatogaphy

Sources & evidence

ORD record: ord-581666fe81c4428aa9b64f8312a00708
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05217964

Reaction notes

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