6-Methyl-1-cyclohexenyl triflate → HCID 10222397, compound

HRID 1794002Notes

Reaction equation

HRID 1794002 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15](C3C=CC(B4OC(C)(C)C(C)(C)O4)=C(C)C=3)=[O:16])[CH2:6][C:5]=12.FC(F)(F)S(O[C:39]1[CH:44]([CH3:45])[CH2:43][CH2:42][CH2:41][CH:40]=1)(=O)=O>>[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:42]3[CH:41]=[CH:40][C:39]([C:8]4[CH:9]([CH3:10])[CH2:11][CH2:12][CH2:13][CH:14]=4)=[C:44]([CH3:45])[CH:43]=3)=[O:16])[CH2:6][C:5]=12

Participants

3

Reactant 2

HCID 110859986-Methyl-1-cyclohexenyl triflateHCID 22219714(10,11-Dihydro-5H-pyrrolo [2,1-c][1,4] benzodiazepin-10-yl)-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone

Product 1

HCID 10222397HCID 10222397, compoundYield 176.5%

Procedure

(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone of Example 2, Step B (0.428 g, 1.00 mmol) and 6-methyl-cyclohex-1-en-1-yl trifluoromethanesulfonate (0.269 g, 1.10 mmol) were reacted in the manner of Example 2, Step C. Purification by flash column chromatography on silica gel, eluting with 20% ethyl acetate in hexane, followed by recrystallization from petroleum ether afforded the title compound (0.350 g) as white crystals, m.p. 132–133° C.

Workup

  1. customPurification by flash column chromatography on silica gel
  2. washeluting with 20% ethyl acetate in hexane
  3. customfollowed by recrystallization from petroleum ether

Sources & evidence

ORD record
ord-75a2b84211e84eb3b9bd5b6f97930b63
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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