HCID 22325119, compound → HCID 69734331, compound

HRID 496053Notes

Reaction equation

HRID 496053 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]([CH:5]1[CH2:7][CH:6]1[O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1)=O>CCOCC>[CH3:1][N:2]([CH3:15])[CH2:3][C@@H:5]1[CH2:7][C@H:6]1[O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1

Participants

3

Reactant 1

HCID 22325119HCID 22325119, compound

Product 1

HCID 69734331HCID 69734331, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

14 g of the compound obtained in Step 1 in 50 ml of ether are slowly added to a suspension of 3.1 g of AlLiH4 in 120 ml of ether. After 16 hours at reflux, the reaction mixture is cooled to 0° C., hydrolysed, filtered and then concentrated under reduced pressure. Chromatography of the residue over silica gel (dichloromethane/methanol: 90/10) allows the expected product to be isolated in a trans/cis diastereoisomeric ratio of 99/1.

Workup

  1. temperatureAfter 16 hours at reflux
  2. filtrationhydrolysed, filtered
  3. concentrationconcentrated under reduced pressure
  4. customto be isolated in a trans/cis diastereoisomeric ratio of 99/1

Sources & evidence

ORD record
ord-a54e3e5a3fd3448fa6de2cd9e3a654ac
Source dataset
uspto-grants-2005_09
Patent number
US06943184B2

Reaction notes

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