1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 90390643, compound

HRID 1056476Notes

Reaction equation

Br[C:2]1[CH:3]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=1.C1CCN2C(=NCCC2)CC1.CCCCCC.CCOC(C)=O>CS(C)=O>[CH:3]1([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]#[C:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a magnetically stirred solution of 6-{[(2E)-2-bromocyclooct-2-en-1-yl]oxy}hexan-1-ol 200 mg (0.658 mmol 1 eq) in dry DMSO (3.5 ml) under Ar atmosphere, DBU (6.58 mmol, 10 eq, 1 ml) were added. The reaction was warmed to 60° C. and was stirred at this temperature for 16 h. Reaction was controlled until complete disappearance of the starting material by TLC (Hexane/AcOEt 7/3 as eluent). The reaction was quenched with a saturated solution of NH4Cl, layers were separated and the aqueous layer was extracted with Et2O (3×20 ml). Combined organic layer was washed with Brine (20 ml), dried over Na2SO4 filtered and concentrated under vacuum. Raw material was purified by chromatography on silica gel column (55 g) (Hexane:AcOEt 7/3) to obtain 6-(cyclooct-2-yn-1-yloxy)hexan-1-ol.

Workup

customReaction
customThe reaction was quenched with a saturated solution of NH4Cl, layers
customwere separated
extractionthe aqueous layer was extracted with Et2O (3×20 ml)
washCombined organic layer was washed with Brine (20 ml)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under vacuum
customRaw material was purified by chromatography on silica gel column (55 g) (Hexane:AcOEt 7/3)

Sources & evidence

ORD record: ord-7b7623e7d1254ead98b3821cce554b48
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399077B2

Reaction notes

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