4,7,7-Trimethyl-3-bicyclo[2.2.1]heptanecarbonyl chloride → HCID 67884844, compound

HRID 1591250Notes

Reaction equation

HRID 1591250 reaction equation
S1C=CN=NC1=[O:7].[CH3:8][N:9]1[C:18]2[C:13](=[CH:14][C:15]([C:19]3[CH:24]([CH3:25])[S:23][CH2:22][NH:21][N:20]=3)=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH2:10]1.[C:26]12([CH3:38])[C:32]([CH3:34])([CH3:33])[CH:29]([CH2:30][CH2:31]1)[CH2:28][CH:27]2[C:35](Cl)=[O:36]>>[C:26]12([CH3:38])[C:32]([CH3:34])([CH3:33])[CH:29]([CH2:30][CH2:31]1)[CH2:28][CH:27]2[C:35]([N:21]1[N:20]=[C:19]([C:15]2[CH:14]=[C:13]3[C:18](=[CH:17][CH:16]=2)[N:9]([CH3:8])[CH2:10][CH2:11][CH2:12]3)[CH:24]([CH3:25])[S:23][C:22]1=[O:7])=[O:36]

Participants

3

Reactant 2

HCID 534427834,7,7-Trimethyl-3-bicyclo[2.2.1]heptanecarbonyl chlorideHCID 67884842HCID 67884842, compound

Product 1

HCID 67884844HCID 67884844, compound

Procedure

Analogously to Example 1, the racemic mixture of 5-[1-methyl-1,2,3,4-tetrahydroquinol-6-yl]-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2 H-1,3,4-thiadiazin-2-one (m.p. 177°) is reacted with (+)-camphanic acid chloride to give 3- [(+)-camphanoyl]-5-(1-methyl-1,2,3, 4-tetrahydroquinol-6-yl)-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one as a mixture of diastereoisomers.

Sources & evidence

ORD record
ord-2a8231e2a0934a909103307ab62d2183
Source dataset
uspto-grants-1993_04
Patent number
US05206363

Reaction notes

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