Aluminium lithium hydride → HCID 68766842, compound

HRID 1374371Notes

Reaction equation

HRID 1374371 reaction equation
[C:1]1([C@@H:7]([NH:9][C@H:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][C@H:11]2[C:23](OC)=[O:24])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[OH:24][CH2:23][C@H:11]1[C@@H:10]([NH:9][C@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH3:8])[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:12]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58745527HCID 58745527, compound

Product 1

HCID 68766842HCID 68766842, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (3R,4S)-1-tert-butyl 3-methyl 4-((S)-1-phenylethylamino)piperidine-1,3-dicarboxylate (47 g, 0.13 mol, See: S. S. Ko, et al, WO PCT 2002002525 for preparation of the enantiomer of this compound) in anhydrous ether (500 mL) at 0° C. was added 1M-LAH (100 mL, 0.1 mol) dropwise, and the mixture was stirred at 0˜15° C. for 3 h. The reaction was quenched with a portion-wise adition of Na2SO4.10H2O (excess) and stirring for 1 h at rt. It was filtered through Celite and the solvent was evaporated off to give (3R,4S)-tert-butyl 3-(hydroxymethyl)-4-((S)-1-phenylethylamino)piperidine-1-carboxylate (quantitative yield).

Workup

  1. customThe reaction was quenched with a portion-wise adition of Na2SO4.10H2O (excess)
  2. stirringstirring for 1 h at rt
  3. filtrationIt was filtered through Celite
  4. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-c12dcaef378e4e6bad927f64e417384f
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

Loading…