HCID 44236097, compound → HCID 66958890, compound

HRID 1244461Notes

Reaction equation

HRID 1244461 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>[CH:19]1([C:11]([OH:17])([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[C:10]([O:9][C@@H:3]2[CH:4]3[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]3)[CH2:2]2)=[O:18])[CH2:23][CH2:22][CH2:21][CH2:20]1

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 from 20.8 g (0.0784 mol) of 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-883c30eaedac4e3ba06bf503e3b7a49d
Source dataset
uspto-grants-2006_10
Patent number
US07122558B2

Reaction notes

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