Ammonium Chloride → tert-Butyl 4-{4-[(E)-2-(naphthalen-1-yl)ethenyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

HRID 549940Notes

Reaction equation

HRID 549940 reaction equation
[C:1]1([CH2:11]P(=O)(OCC)OCC)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[CH:26]([C:28]1[N:29]=[C:30]([CH:33]2[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35][CH2:34]2)[S:31][CH:32]=1)=O.[Cl-].[NH4+]>O1CCCC1>[C:1]1(/[CH:11]=[CH:26]/[C:28]2[N:29]=[C:30]([CH:33]3[CH2:34][CH2:35][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:37][CH2:38]3)[S:31][CH:32]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 101271Diethyl P-(1-naphthalenylmethyl)phosphonateHCID 7172298tert-Butyl 4-(4-formyl-1,3-thiazol-2-yl)piperidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 67156264tert-Butyl 4-{4-[(E)-2-(naphthalen-1-yl)ethenyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under argon, diethyl 1-naphthylmethylphosphonate (1.88 g) is dissolved in tetrahydrofuran (20 ml) and cooled to 0° C. 757 mg of potassium tert-butoxide are added, whereupon the colour of the solution changes to dark-red. After a further 10 min of stirring, tert-butyl 4-(4-formyl-1,3-thiazol-2-yl)piperidine-1-carboxylate (1.00 g) is added. The mixture is stirred at 0° C. for 30 min and then warmed to room temperature. After a further 20 min, conc. ammonium chloride solution is added. The aqueous phase is separated off and extracted with ethyl acetate. The combined organic phases are dried over sodium sulphate and concentrated, and the residue is purified chromatographically. This gives tert-butyl 4-{4-[(E)-2-(naphthalen-1-yl)ethenyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (1.16 g) as the E isomer.

Workup

  1. stirringThe mixture is stirred at 0° C. for 30 min
  2. temperaturewarmed to room temperature
  3. waitAfter a further 20 min
  4. customThe aqueous phase is separated off
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic phases are dried over sodium sulphate
  7. concentrationconcentrated
  8. customthe residue is purified chromatographically

Sources & evidence

ORD record
ord-78d65777f73d4aaeb2ac242c988b1a71
Source dataset
uspto-grants-2011_05
Patent number
US07943774B2

Reaction notes

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