1-(2-tert-Butoxycarbonylamino-thiazol-5-ylmethyl)-piperidine-4-carboxylic acid ethyl ester → 1-(2-Amino-thiazol-5-ylmethyl)-piperidine-4-carboxylic acid ethyl ester

HRID 1889186Notes

Reaction equation

HRID 1889186 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[S:17][C:16]([NH:18]C(OC(C)(C)C)=O)=[N:15][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:7][CH2:8][N:9]([CH2:12][C:13]2[S:17][C:16]([NH2:18])=[N:15][CH:14]=2)[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 596100481-(2-tert-Butoxycarbonylamino-thiazol-5-ylmethyl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 596100451-(2-Amino-thiazol-5-ylmethyl)-piperidine-4-carboxylic acid ethyl esterYield 84%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent2×

Procedure

To a stirred solution of 1-(2-tert-Butoxycarbonylamino-thiazol-5-ylmethyl)-piperidine-4-carboxylic acid ethyl ester (0.98 g) in 2 ml of DCM, 10 ml TFA was added at room temperature and reaction mixture was stirred for 12 hrs. After completion of reaction TFA was removed under reduced pressure. The residue was taken in ethyl acetate (25 ml), and neutralized by aqueous saturated sodium bicarbonate. Organic layer was separated and aqueous layer was further extracted with ethyl acetate (25 ml). Combined organic layer was washed with water (25 ml) followed by brine (25 ml). Organic layer was dried over anhydrous sodium sulfate, sodium sulfate was filtered and washed with ethyl acetate (10 ml) and solvent was evaporated using rotavapour to get required product as solid which was dried under vacuum (2 mbar) for 2 hours. The crude yellow solid material was used for the next step with out any further purification, (0.6 g, and 84% yield).

Workup

  1. customreaction mixture
  2. customwas removed under reduced pressure
  3. customOrganic layer was separated
  4. extractionaqueous layer was further extracted with ethyl acetate (25 ml)
  5. washCombined organic layer was washed with water (25 ml)
  6. dry with materialOrganic layer was dried over anhydrous sodium sulfate, sodium sulfate
  7. filtrationwas filtered
  8. washwashed with ethyl acetate (10 ml) and solvent
  9. customwas evaporated

Sources & evidence

ORD record
ord-706ddbe8dac0484482f3190595fff367
Source dataset
uspto-grants-2013_08
Patent number
US08501955B2

Reaction notes

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