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Benzylamine → tert-Butyl 4-(benzylamino)-3,3-difluoropiperidine-1-carboxylate

HRID 2280374
Notes
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Reaction equation

HRID 2280374 reaction equation
[F:1][C:2]1([F:16])[C:7](=O)[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:17]([NH:24][CH:7]1[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3][C:2]1([F:16])[F:1])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 56776981tert-Butyl 3,3-difluoro-4-oxopiperidine-1-carboxylate

Product 1

HCID 66710726tert-Butyl 4-(benzylamino)-3,3-difluoropiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of tert-butyl 3,3-difluoro-4-oxopiperidine-1-carboxylate (0.250 g, 1.06 mmol) in CH2Cl2 (4.5 mL) was added benzylamine (0.13 mL, 1.17 mmol) and sodium triacetoxyborohydride (0.356 g, 1.59 mmol) and the solution was stirred at rt for 22 h. The reaction mixture was treated with sat. aq. Na2CO3 and extracted with EA (3×50 mL). The combined organic extracts were dried over MgSO4, filtered, and the solvent removed under reduced pressure. The residue was purified by FC (Heptane/EA, 1:1) to give tert-butyl 4-(benzylamino)-3,3-difluoropiperidine-1-carboxylate. LC-MS-conditions 08: tR=0.65 min; [M+H]+=327.32.

Workup

  1. extractionextracted with EA (3×50 mL)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customThe residue was purified by FC (Heptane/EA, 1:1)

Sources & evidence

ORD record
ord-4499ac85e7464dd28838beef3fef46b6
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09139524B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes