Diisopropylethylamine → tert-butyl (3S)-3-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperidin-1-yl)methyl]piperidine-1-carboxylate

HRID 603238Notes

Reaction equation

HRID 603238 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:10][C:11]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:12])[CH:6]=[CH:7][C:8]=1[Cl:9].C(N(C(C)C)CC)(C)C.[CH:28]([C@@H:30]1[CH2:35][CH2:34][CH2:33][N:32]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:31]1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:2][C:3]1[CH:4]=[C:5]([NH:10][C:11]([CH:13]2[CH2:14][CH2:15][N:16]([CH2:28][C@@H:30]3[CH2:35][CH2:34][CH2:33][N:32]([C:36]([O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:37])[CH2:31]3)[CH2:17][CH2:18]2)=[O:12])[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 42325667tert-Butyl (3R)-3-formylpiperidine-1-carboxylateHCID 54595048N-(3,4-dichlorophenyl)piperidine-4-carboxamide hydrochloride

Product 1

HCID 57656896tert-butyl (3S)-3-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperidin-1-yl)methyl]piperidine-1-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of N-(3,4-dichlorophenyl)piperidine-4-carboxamide hydrochloride (1.55 g) in dichloromethane (100 mL) was added di-iso-propylethylamine (1.3 mL). The solution was stirred for 15 minutes after which tert-butyl (3R)-3-formylpiperidine-1-carboxylate (1.17 g) and sodium triacetoxyborohydride (1.59 g) was added. The reaction was stirred at room temperature overnight. The reaction mixture was partitioned between dichloromethane and water and the aqueous layer extracted with dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate and evaporated to give the title compound as a white foam (2.34 g, 100%).

Workup

  1. additionwas added
  2. customThe reaction mixture was partitioned between dichloromethane and water
  3. extractionthe aqueous layer extracted with dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-5db280a4c7c04be493b5347248068eac
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

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