Ammonium Chloride → HCID 68765812, compound

HRID 1171648Notes

Reaction equation

HRID 1171648 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11]/[C:10]/1=[CH:34]\[C:35](OCC)=[O:36])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+]>ClCCl.C1(C)C=CC=CC=1>[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:11]/[C:10]/1=[CH:34]\[CH2:35][OH:36])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 23138644HCID 23138644, compound

Product 1

HCID 68765812HCID 68765812, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-4-(t-butyldimethylsilyloxy)-3-[(ethoxycarbonyl)methylidene]-1-(triphenylmethyl)piperidine (15.14 g) in dichloromethane (110 ml) was added dropwise a 1.01N solution of diisobutyl aluminium hydride in toluene (66.40 ml) at −70° C., and the resulting mixture was stirred at the same temperature for 3 hours. After stirring, saturated aqueous ammonium chloride solution was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, and the organic layer was dried over anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:3) as the eluent to afford the title compound (13.22 g, yield: 95%) as a colourless amorphous solid.

Workup

  1. stirringAfter stirring
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium chloride solution
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-86590845495f4edb885b85aab6134ce5
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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