Acetic Acid → HCID 66589770, compound

HRID 16891Notes

Reaction equation

HRID 16891 reaction equation
C(O[BH-](O[C:11](=O)[CH3:12])OC(=O)C)(=O)C.[Na+].[N:15]1([C:22]2[S:26][C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:24][CH:23]=2)[CH2:21][CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.[C:32](O)(=O)C>CC(C)=O>[CH:11]([N:18]1[CH2:19][CH2:20][CH2:21][N:15]([C:22]2[S:26][C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:24][CH:23]=2)[CH2:16][CH2:17]1)([CH3:12])[CH3:32]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 66589905HCID 66589905, compound

Product 1

HCID 66589770HCID 66589770, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Sodium triacetoxyborohydride (396 mg, 1.87 mmol) was added portionwise to ethyl 5-(1,4-diazepan-1-yl)thiophene-2-carboxylate (190 mg, 0.75 mmol) and acetic acid (0.086 ml, 1.49 mmol) in acetone (1.917 ml) at room temperature. The resulting solution was stirred at ambient temperature for 18 h under nitrogen. The reaction mixture was concentrated and diluted with water (200 mL) and basified with 2M NaOH. The aqueous was extracted with diethyl ether (3×100 mL) and washed sequentially with water (200 mL) and saturated brine (200 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford desired product ethyl 5-(4-isopropyl-1,4-diazepan-1-yl)thiophene-2-carboxylate (181 mg, 82%). This was used directly with no further purification.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water (200 mL)
  3. extractionThe aqueous was extracted with diethyl ether (3×100 mL)
  4. washwashed sequentially with water (200 mL) and saturated brine (200 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-0f400b412b314ba4b18f55860a0a6183
Source dataset
uspto-grants-2010_06
Patent number
US07737149B2

Reaction notes

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