Hydrochloric Acid → Z-(1S,6S)-7-naphthalen-2-ylmethyl-7,9-diaza-bicyclo[4.2.2]dec-3-ene

HRID 40628Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][N:12]1[C:19](=O)[C@H:18]2[NH:21][C:22](=O)[C@@H:13]1[CH2:14][CH:15]=[CH:16][CH2:17]2.CC(C[AlH]CC(C)C)C.Cl>C(OCC)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][N:12]1[CH2:19][C@H:18]2[NH:21][CH2:22][C@@H:13]1[CH2:14][CH:15]=[CH:16][CH2:17]2

Participants

Conditions

Temperature: 130 °C

Procedure

Z-(1S,6S)-7-naphthalen-2-ylmethyl-7,9-diaza-bicyclo[4.2.2]dec-3-ene-8,10-dione (40 mg, 0.1307 mmol) was placed in a μW tube, followed by addition of DiBAl-H (3 mL, 3 mmol, [1M] in THF). The reaction mixture was purged under argon for 20 min, then heated to 130° C. for 900 sec. The reaction mixture was poured in to a 100 mL mixture (1:1) of Rochelle's solution and diethyl ether and stirred vigorously overnight. The reaction mixture was separated and the organic layer was dried with magnesium sulfate, filtered and the solvent evaporated under reduced pressure to yield an oil. The oil was treated with 1M HCl in diethyl ether (2 mL) to yield the title compound as a residue.

Workup

customThe reaction mixture was purged under argon for 20 min
additionThe reaction mixture was poured in to a 100 mL mixture (1:1) of Rochelle's solution and diethyl ether
customThe reaction mixture was separated
dry with materialthe organic layer was dried with magnesium sulfate
filtrationfiltered
customthe solvent evaporated under reduced pressure
customto yield an oil

Sources & evidence

ORD record: ord-959ee6e48f0942c6b41092be23dfc88b
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530475B2

Reaction notes

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