HCID 21180664, compound → HCID 21180827, compound

HRID 1386715Notes

Reaction equation

HRID 1386715 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([C:28](OCC)=[O:29])([C:23](OCC)=[O:24])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([CH2:23][OH:24])([CH2:28][OH:29])[CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 21180664HCID 21180664, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21180827HCID 21180827, compoundYield 59%

Procedure

A mixture of 430 mg (1.0 mmol) of 1-benzyl-4-(3-phenyl-2,2-bis(carboethoxy)propyl)piperidine (from EXAMPLE 32, Step D) and 65 mg (1.7 mmol) of lithium aluminum hydride was heated at reflux for 1 h. The reaction was cooled and quenched with 10 mL of 1.0 N NaOH. The quenched mixture was partitioned between 50 mL of ether and 25 mL of H2O and the layers were separated. The organic layer was dried over MgSO4 and concentrated. The resulting solid was triturated with ether, filtered and dried to afford 204 mg (59%) of the title compound: 1H NMR (500 MHz) δ 1.16 (d, J=5.0,2H), 1.32-1.36 (m, 2H), 1.45-1.49 (m, 1H), 1.66 (d, J=12.0, 2H), 1.76 (br s, 2H), 1.97 (app t, J=11.5, 2H), 2.40 (br s, 2H), 2.73 (s, 2H), 2.83 (app d, J=11.5, 2H), 3.48 (s, 2H), 3.58 (ABq, J=10.5, 4H), 7.19-7.31 (10H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. temperatureThe reaction was cooled
  4. customquenched with 10 mL of 1.0 N NaOH
  5. customThe quenched mixture was partitioned between 50 mL of ether and 25 mL of H2O
  6. customthe layers were separated
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated
  9. customThe resulting solid was triturated with ether
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-e456037d430145d3a5bb9bef5039f238
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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