Sodium t-butoxide → HCID 58478442, compound

HRID 1911079Notes

Reaction equation

HRID 1911079 reaction equation
C([O:3][C:4]([C:6]1([CH2:19][CH2:20][CH2:21][NH:22][C:23]2[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][C:24]=2[CH3:30])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=O)C.CC([O-])(C)C.[Na+]>C1COCC1>[C:15]([O:14][C:12]([N:9]1[CH2:10][CH2:11][C:6]2([C:4](=[O:3])[N:22]([C:23]3[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][C:24]=3[CH3:30])[CH2:21][CH2:20][CH2:19]2)[CH2:7][CH2:8]1)=[O:13])([CH3:16])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 23676156Sodium t-butoxideHCID 58478421HCID 58478421, compound

Product 1

HCID 58478442HCID 58478442, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-[3-(4-Bromo-2-methyl-phenylamino)-propyl]-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (3.78 g, 7.81 mmol, 1 eq) was dissolved in THF (80 mL). A 1M solution of NaOt-Bu in THF (7.8 mL, 7.8 mmol, 1 eq) was added and the reaction mixture was stirred for 2 h at rt. The reaction mixture was stirred for 48 h, quenched with 250 mL of water, transferred to a separatory funnel and extracted with dichloromethane (2×150 mL). The combined organics were dried over Na2SO4 and purified by column chromatography on silica gel (200 g column, 50% EtOAc in heptanes; 50 mL/min). This gave 2.49 g (73%) of the title compound as a beige gum.

Workup

  1. stirringThe reaction mixture was stirred for 48 h
  2. customquenched with 250 mL of water
  3. customtransferred to a separatory funnel
  4. extractionextracted with dichloromethane (2×150 mL)
  5. dry with materialThe combined organics were dried over Na2SO4
  6. custompurified by column chromatography on silica gel (200 g column, 50% EtOAc in heptanes; 50 mL/min)

Sources & evidence

ORD record
ord-4adc6e715841482c8f68bac17cb6a815
Source dataset
uspto-grants-2013_12
Patent number
US08604046B2

Reaction notes

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