Ammonium Hydroxide → HCID 66790139, compound

HRID 1510166Notes

Reaction equation

HRID 1510166 reaction equation
[CH3:1][CH:2]1[CH2:7][C:6](=O)[CH2:5][CH2:4][N:3]1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[CH:19]([S:22]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[C:32]([NH2:37])=[CH:33][CH:34]=[CH:35][CH:36]=2)=[CH:27][CH:26]=1)(=[O:24])=[O:23])([CH3:21])[CH3:20].C[Si]([C:42]#[N:43])(C)C.[OH-].[NH4+]>C(O)(=O)C>[C:42]([C:6]1([NH:37][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[C:28]2[CH:29]=[CH:30][C:25]([S:22]([CH:19]([CH3:21])[CH3:20])(=[O:24])=[O:23])=[CH:26][CH:27]=2)[CH2:5][CH2:4][N:3]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH:2]([CH3:1])[CH2:7]1)#[N:43]

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 82115Trimethylsilyl cyanideHCID 46941997Benzyl 2-methyl-4-oxopiperidine-1-carboxylateHCID 66790844HCID 66790844, compound

Product 1

HCID 66790139HCID 66790139, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of benzyl 2-methyl-4-oxopiperidine-1-carboxylate (1.97 g, 7.95 mmol) and 4′-(isopropylsulfonyl)biphenyl-2-amine (2.19 g, 7.95 mmol) in acetic acid (25 mL) was added trimethylsilyl cyanide (0.79 g, 7.95 mmol). After stirring the reaction at rt overnight the reaction was poured into an icy solution of ammonium hydroxide (30 mL). The solution was extracted with chloroform (three times), dried over MgSO4 and concentrated under vacuum. Purification by silica gel chromatography afforded the desired product. To enhance the cis/trans product ratio the isolated material was dissolve in methanol (20 mL) and trimethylsilyl cyanide (3.18 g, 23.9 mmol) was added. After stirring the reaction at 70° C. overnight the reaction was concentrated under vacuum. Purification by silica gel chromatography afforded the desired product.

Workup

  1. customthe reaction at rt overnight the reaction
  2. extractionThe solution was extracted with chloroform (three times)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuum
  5. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-6b81607b0b0845d796e5c5c096663e96
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

Loading…