2-Bromo-6-methoxynaphthalene → 3-Azaspiro[5.5]undec-8-ene, 9-(6-methoxy-2-naphthalenyl)-

HRID 419277Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[CH:3]=1.[Li]C(C)(C)C.C(OC([N:26]1[CH2:31][CH2:30][C:29]2([CH2:36][CH2:35][C:34](=O)[CH2:33][CH2:32]2)[CH2:28][CH2:27]1)=O)(C)(C)C>C1COCC1>[CH3:13][O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([C:34]1[CH2:35][CH2:36][C:29]3([CH2:30][CH2:31][NH:26][CH2:27][CH2:28]3)[CH2:32][CH:33]=1)[CH:11]=[CH:10]2

Participants

Conditions

Temperature: -40 °C

Procedure

Was prepared according to method A with the following variation: To a solution of 2-bromo-6-methoxynaphthalen in dry THF (30 mL) cooled to −40° C., tert-BuLi (1.5 M in pentane (5.55 mL)) was added drop-wise. The mixture was stirred for 1 h at −40° C. and then allowed to warm up to −10° C. 9-Oxo-3-aza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester (495 mg, 1.85 mmol) in dry THF (10 mL) was added drop-wise and stirred for 3 h at 0° C. Beige solid. Mp. 146.9-149.5° C.

Workup

customWas prepared
temperatureto warm up to −10° C
stirringstirred for 3 h at 0° C

Sources & evidence

ORD record: ord-a536c83c010b4f8cb2232cd6b6a91431
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093388B2

Reaction notes

Loading…