Acetic Acid → Tert-butyl (R)-2-phenyl-2-(piperidin-1-YL)acetate

HRID 923411Notes

Reaction equation

HRID 923411 reaction equation
Cl.[NH2:2][C@H:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].C([BH3-])#N.C(O)(=O)C.[CH:24](=O)[CH2:25][CH2:26][CH2:27][CH:28]=O>CO.C(Cl)Cl.O>[C:11]1([C@@H:3]([N:2]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 3485GlutaraldehydeHCID 498716Cyano-borohydrideHCID 56777188H-D-Phg-otbu hcl

Product 1

HCID 59166413Tert-butyl (R)-2-phenyl-2-(piperidin-1-YL)acetate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a slurry of (R)-tert-butyl 2-amino-2-phenylacetate HCL (Chem-Impex, 0.200 g, 0.821 mmol), MP-cyanoborohydride (2.44 mmol/g; 500 mg) and acetic acid (0.141 mL, 2.462 mmol) in MeOH (2.00 mL) and CH2Cl2 (2 mL) at rt was added glutaraldehyde (0.155 mL, 0.821 mmol) as a 50% solution in water. The reaction was stirred for 30 min., the reaction filtered, washed with MeOH and concentrated. The residue was taken up in CH2Cl2, washed with saturated NaHCO3, dried (Na2SO4) and concentrated to give the title compound. MS (DCI; M+H) m/z=276.

Workup

  1. filtrationthe reaction filtered
  2. washwashed with MeOH
  3. concentrationconcentrated
  4. washwashed with saturated NaHCO3
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-57f9213d03974fb2ba99a31cc001e0b6
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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