HCID 44236097, compound → HCID 66958890, compound

HRID 1366725Notes

Reaction equation

HRID 1366725 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:18])[C:11](=[O:17])[C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)[CH2:2]2.[CH:19]1([Mg]Cl)[CH2:23][CH2:22][CH2:21][CH2:20]1>CCOCC>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:18])[C:11]([CH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)([OH:17])[C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)[CH2:2]2

Participants

4

Reactant 2

HCID 44236097HCID 44236097, compoundHCID 178478989HCID 178478989, compound

Product 1

HCID 66958890HCID 66958890, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Prepared using the same method as for Intermediate I-14, but from 20.8 g (0.0784 mol) of 2-oxo-2-thien-2-ylacetic acid (3R)-1-azabicyclo[2.2.2]oct-3-yl ester and cyclopentylmagnesium cloride, 0.08 mol (40 ml of a solution 2M in ether). The oil obtained (15.64 g) was purified by chromatography on silica gel eluting with chloroform/methanol/ammonia 97:3:0.5 to obtain 8.38 g (32%) of a pure product, mixture of diastereomers: I-15a and I-15b. Structure confirmed by 1H-NMR.

Workup

  1. customPrepared
  2. customThe oil obtained (15.64 g)
  3. customwas purified by chromatography on silica gel eluting with chloroform/methanol/ammonia 97:3:0.5
  4. customto obtain

Sources & evidence

ORD record
ord-7c8b59d0bd254882934f055723178359
Source dataset
uspto-grants-2011_02
Patent number
US07893087B2

Reaction notes

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