Sodium Iodide → HCID 117856688, compound

HRID 509916Notes

Reaction equation

HRID 509916 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][CH2:11][NH:10][CH2:9]1)(C)(C)C.[CH2:15]([O:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][Cl:28])=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:31]([O-:34])([O-])=O.[K+].[K+].[Na+].[I-]>CS(C)=O>[Cl-:28].[NH2:7][C@H:8]1[CH2:13][CH2:12][CH2:11][N+:10]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:34][CH2:31][C:24]3[CH:23]=[CH:30][CH:29]=[CH:26][CH:25]=3)=[CH:20][CH:21]=2)([CH2:27][C:26]2[CH:29]=[CH:30][C:23]([O:22][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:24][CH:25]=2)[CH2:9]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 700424-Benzyloxybenzyl chlorideHCID 1514171tert-butyl N-[(3S)-piperidin-3-yl]carbamate

Product 1

HCID 117856688HCID 117856688, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(S)-Piperidin-3-yl-carbamic acid tert-butyl ester (150 mg), 4-benzyloxybenzyl chloride (383 mg), K2CO3 (227 mg) and NaI (34 mg) are stirred in dimethylsulfoxide (5 mL) for 16 h. Volatiles are evaporated in vacuo, the residue partitioned between water and ethyl acetate, the organic phase collected, dried (Na2SO4) and volatiles evaporated in vacuo to give 540 mg of crude product that is used without further purification. To the material thus obtained dichloromethane (15 mL) and trifluoroacetic acid (0.56 mL) are added. After 16 h at room temperature volatiles are evaporated in vacuo, methanolic NH3 is added until a slightly basic pH is reached, volatiles are again evaporated and the residue is purified by chromatography (silica gel, dichloromethane:MeOH containing NH3OH gradient of increasing polarity) to give the title compound. Yield 110 mg.

Workup

  1. customVolatiles are evaporated in vacuo
  2. customthe residue partitioned between water and ethyl acetate
  3. customthe organic phase collected
  4. dry with materialdried (Na2SO4)
  5. customvolatiles evaporated in vacuo
  6. customto give 540 mg of crude product that
  7. customis used without further purification
  8. additionTo the material thus obtained dichloromethane (15 mL) and trifluoroacetic acid (0.56 mL) are added
  9. customAfter 16 h at room temperature volatiles are evaporated in vacuo, methanolic NH3
  10. additionis added until a slightly basic pH
  11. customvolatiles are again evaporated
  12. customthe residue is purified by chromatography (silica gel, dichloromethane:MeOH containing NH3OH gradient of increasing polarity)

Sources & evidence

ORD record
ord-87828d5cc8a241c38463a67529b5221e
Source dataset
uspto-grants-2015_08
Patent number
US09096548B2

Reaction notes

Loading…