Methyl (8-methyl-8-azabicyclo[3.2.1]octan-3-ylidene)acetate → HCID 11393014, compound

HRID 1786287Notes

Reaction equation

CO[C:3](=[O:14])[CH:4]=[C:5]1[CH2:11][CH:10]2[N:12]([CH3:13])[CH:7]([CH2:8][CH2:9]2)[CH2:6]1.[C:15]1([Mg]Cl)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH3:13][N:12]1[CH:7]2[CH2:8][CH2:9][CH:10]1[CH2:11][C:5](=[CH:4][C:3]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[OH:14])[CH2:6]2

Participants

Reactant 2

HCID 13670649Methyl (8-methyl-8-azabicyclo[3.2.1]octan-3-ylidene)acetate

HCID 178478979HCID 178478979, compound

Product 1

HCID 11393014HCID 11393014, compound

Procedure

The title compound was prepared from (8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-acetic acid methyl ester and phenylmagnesium chloride by following the experimental procedures in Example 1 (44% yield): LCMS (ES) m/z 320 (M+H)+; 1H-NMR(CDCl3) δ 1.20 (m, 1H), 1.54 (m, 1H), 1.70 (m, 1H), 1.77 (m, 1H), 1.93 (m, 1H), 2.04 (m, 1H), 2.26 (s, 3H), 2.35 (m, 1H), 2.71 (m, 1H), 2.97 (m, 1H), 3.19 (m, 1H), 6.14 (s, 1H), 7.21 (m, 2H), 7.30 (m, 4H), 7.45 (m, 2H), 7.53 (m, 2H).

Sources & evidence

ORD record: ord-98bcc45c4c96452387c7b29229477e69
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507747B2

Reaction notes

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