tert-Butyl 4-oxopiperidine-1-carboxylate → 4-(4-Methylsulfanyl-3-trifluoromethyl-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 511085Notes

Reaction equation

HRID 511085 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[C:10]([F:13])([F:12])[F:11].[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[C:4]([C:10]([F:11])([F:12])[F:13])[CH:5]=2)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 219046854-(Methylsulfanyl)-3-(trifluoromethyl)aniline

Product 1

HCID 585761814-(4-Methylsulfanyl-3-trifluoromethyl-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Methylsulfanyl-3-trifluoromethyl-phenylamine (828 mg; 4.00 mmol), 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (876 mg; 4.40 mmol) and sodium triacetoxyborohydride (2.52 g; 12.00 mmol) are suspended in dichloromethane (18 mL) and the resulting mixture is stirred for 1 day. The suspension is then diluted with dichloromethane (50 mL) and is washed with water (30 mL) and aq. sat. ammonium chloride (3×30 mL). The organic phase is dried over magnesium sulphate, filtered and concentrated under reduced pressure to deliver the desired product in the presence of remaining traces of solvent (1.8 g; 4.6 mmol).

Workup

  1. washis washed with water (30 mL) and aq. sat. ammonium chloride (3×30 mL)
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-65938e0dc333447da39704933ec5e5b3
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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