1-Iodopentane → HCID 11208062, compound

HRID 1759783Notes

Reaction equation

[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([NH2:14])[CH:5]=[CH:4][C:3]1=2.C([Li])CCC.I[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:22]([NH:14][C:6]1[CH:5]=[CH:4][C:3]2[C:2]([CH3:15])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=2[CH:7]=1)[CH2:23][CH2:24][CH2:25][CH3:26]

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-ylamine (1) (1.0 g, 4.93 mmole) in 12 mL tetrahydrofuran (THF) was cooled to −78° C. and treated dropwise with 2.5 M n-butyllithium solution (2.2 mL) and allowed to warm to −20° C. over a one hour period. Iodopentane (1.28 mL) was introduced at −20° C., the mixture stirred at room temperature for three hours, poured into 50 mL of a saturated aqueous sodium bicarbonate solution and extracted with three portions of 50 mL of ether. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give a brown oil. The product was purified by flash chromatography (SiO2, 5% ethyl acetate/hexanes) providing 1.1 g (82%) of pentyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine (51) as a colorless oil.

Workup

extractionextracted with three portions of 50 mL of ether
dry with materialThe combined organic extracts were dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto give a brown oil
customThe product was purified by flash chromatography (SiO2, 5% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-af39b1556c0f4f6297cbf88dd71a946a
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06838472B2

Reaction notes

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