Acetic Anhydride → HCID 58478421, compound

HRID 1516375Notes

Reaction equation

HRID 1516375 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([Br:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH2:10]([O:12][C:13]([C:15]1([CH2:28][CH2:29][CH:30]=O)[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)=[O:14])[CH3:11].C(OC(=O)C)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH2:10]([O:12][C:13]([C:15]1([CH2:28][CH2:29][CH2:30][NH:4][C:3]2[CH:5]=[CH:6][C:7]([Br:9])=[CH:8][C:2]=2[CH3:1])[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)=[O:14])[CH3:11]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 114234-Bromo-2-methylanilineHCID 5049666Sodium triacetoxyborohydrideHCID 58478452HCID 58478452, compound

Product 1

HCID 58478421HCID 58478421, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

2-Methyl-4-bromo-aniline (1.68 g, 9.05 mmol, 1 eq) was dissolved in 1,2-dichloroethane (95 mL). A solution of 4-(3-Oxo-propyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (2.8 g, 9.05 mmol, 1 eq) in 95 mL of 1,2-dichloroethane was added to the previous solution followed by glacial acetic anhydride (1.74 g, 28.05 mol, 3.1 eq) and NaBH(OAc)3 (5.76 g, 27.15 mmol, 3 eq). The reaction mixture was stirred for 48 h, quenched with 200 mL of water, transferred to a separatory funnel and extracted with dichloromethane (2×100 mL). The combined organics were dried over Na2SO4 and purified by column chromatography on silica gel (200 g column, 25% EtOAc in heptanes; 50 mL/min). This gave 3.78 g (86%) of the title compound as a beige gum.

Workup

  1. customquenched with 200 mL of water
  2. customtransferred to a separatory funnel
  3. extractionextracted with dichloromethane (2×100 mL)
  4. dry with materialThe combined organics were dried over Na2SO4
  5. custompurified by column chromatography on silica gel (200 g column, 25% EtOAc in heptanes; 50 mL/min)

Sources & evidence

ORD record
ord-e6c6468e3a074c26852dde9ba9c419cb
Source dataset
uspto-grants-2012_07
Patent number
US08227481B2

Reaction notes

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