HCID 11234748, compound → HCID 86586408, compound

HRID 494873Notes

Reaction equation

HRID 494873 reaction equation
CON(C)[C:4](=[O:28])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17]([CH2:19][CH2:20][N:21]4[CH2:25][CH2:24][CH2:23][C@H:22]4[CH3:26])=[CH:16][C:15]=3[CH:27]=2)[CH:6]=1.C1([Mg]Br)CCCC1>>[CH3:26][C@@H:22]1[CH2:23][CH2:24][CH2:25][N:21]1[CH2:20][CH2:19][C:17]1[O:18][C:14]2[CH:13]=[CH:12][C:11]([C:7]3[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=3)[CH:4]=[O:28])=[CH:27][C:15]=2[CH:16]=1

Participants

3

Reactant 2

HCID 11234748HCID 11234748, compoundHCID 178419650HCID 178419650, compound2×

Product 1

HCID 86586408HCID 86586408, compoundYield 16%

Procedure

The product from Example 145 and cyclopentylmagnesium bromide were processed as described in Example 146, except that additional cyclopentylmagnesium bromide was added after the reaction had stirred overnight (400 mol %) and after another four hours (600 mol %). The reaction mixture was allowed to stir for three additional days (16% yield). MS (ESI APCI) m/z 334 (M+H)+; 1HNMR (300 MHz, CD3OD) δ 1.17 (d, 3H), 1.38-1.53 (m, 1H), 1.77-1.86 (m, 2H), 1.94-2.08 (m, 1H), 2.23-2.34 (m, 1H), 2.40-2.59 (m, 2H), 2.94-3.15 (m, 2H), 3.19-3.34 (m, 2H), 6.63 (d, 1H), 7.51-7.54 (m, 2H), 7.65 (dd, 1H), 7.80 (dd, 1H), 7.87 (ddd, 1H), 7.96 (ddd, 1H), 8.16 (dd, 1H), 10.07 (s, 1H).

Workup

  1. additionwas added after the reaction
  2. waitafter another four hours (600 mol %)
  3. stirringto stir for three additional days (16% yield)

Sources & evidence

ORD record
ord-523ecc7de8d542c9a54d8757ed3b71ef
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Reaction notes

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