Acetic Acid → tert-Butyl 4-carbamoyl-4-[(3,3,3-trifluoropropyl)amino]piperidine-1-carboxylate

HRID 450501Notes

Reaction equation

HRID 450501 reaction equation
[NH2:1][C:2]1([C:15](=[O:17])[NH2:16])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[F:18][C:19]([F:24])([F:23])[CH2:20][CH:21]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>O.C(Cl)Cl>[C:15]([C:2]1([NH:1][CH2:21][CH2:20][C:19]([F:24])([F:23])[F:18])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4][CH2:3]1)(=[O:17])[NH2:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 680283,3,3-TrifluoropropanalHCID 5049666Sodium triacetoxyborohydrideHCID 10562199tert-Butyl 4-amino-4-carbamoylpiperidine-1-carboxylate

Product 1

HCID 86656052tert-Butyl 4-carbamoyl-4-[(3,3,3-trifluoropropyl)amino]piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

10 g of tert-butyl 4-amino-4-carbamoylpiperidine-1-carboxylate, 4.42 g of 3,3,3-trifluoropropionaldehyde, 17.61 g of sodium triacetoxyborohydride and 4.51 ml of acetic acid are added, at AT, to 250 ml of DCM, and then the mixture is stirred for 3 hours. Water is added and the expected compound is extracted with DCM, and the organic phase is washed with a saturated solution of NaHCO3 and then with water. After drying of the organic phase, filtration and evaporation to dryness, 13 g of expected compound are obtained.

Workup

  1. extractionthe expected compound is extracted with DCM
  2. washthe organic phase is washed with a saturated solution of NaHCO3
  3. dry with materialAfter drying of the organic phase, filtration and evaporation to dryness, 13 g of expected compound
  4. customare obtained

Sources & evidence

ORD record
ord-dc4b5a2019064ab18a8c81df11c75499
Source dataset
uspto-grants-2013_07
Patent number
US08486971B2

Reaction notes

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