Triethyl phosphite → diethyl [(6S*,9aR*)-6-(4-methoxyphenyl)-4-oxooctahydroquinolizin-3-yl]phosphonate

HRID 553881Notes

Reaction equation

HRID 553881 reaction equation
I[CH:2]1[C:11](=[O:12])[N:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][C@@H:9]2[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH2:4][CH2:3]1.[P:21]([O:28]CC)([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24]>>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C@@H:9]2[CH2:8][CH2:7][CH2:6][C@H:5]3[N:10]2[C:11](=[O:12])[CH:2]([P:21](=[O:28])([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24])[CH2:3][CH2:4]3)=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 69077527(6R*,9aS*)-3-iodo-6-(4-methoxyphenyl)octahydroquinolizin-4-one

Product 1

HCID 86612697diethyl [(6S*,9aR*)-6-(4-methoxyphenyl)-4-oxooctahydroquinolizin-3-yl]phosphonate

Conditions

Temperature
120 °C

Procedure

A mixture of (6R*,9aS*)-3-iodo-6-(4-methoxyphenyl)octahydroquinolizin-4-one (34 mg) with triethyl phosphite (1 mL) was stirred at 120° C. for five hours. The reaction solution was left to cool to room temperature and then concentrated under reduced pressure to obtain 35 mg of the title compound. The property value of the compound is as follows.

Workup

  1. waitThe reaction solution was left
  2. temperatureto cool to room temperature
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0b923a222400495fac9778f9c9723174
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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