Ammonium formate → 6-Hydroxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]-2-[4-[4-methoxy-4-oxobutoxy]phenyl]benzo[b]thiophene

HRID 1595043Notes

Reaction equation

HRID 1595043 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:16]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[C:20]([O:30][CH3:31])[CH:19]=3)=[C:15]([C:32]3[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][CH2:41][C:42]([O:44][CH3:45])=[O:43])=[CH:34][CH:33]=3)[S:14][C:13]=2[CH:46]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C1COCC1.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[C:16]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[C:20]([O:30][CH3:31])[CH:19]=3)=[C:15]([C:32]3[CH:33]=[CH:34][C:35]([O:38][CH2:39][CH2:40][CH2:41][C:42]([O:44][CH3:45])=[O:43])=[CH:36][CH:37]=3)[S:14][C:13]=2[CH:46]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 217063264-[4-[6-Benzyloxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]benzo[b]thiophen-2-yl]phenoxy]butanoic acid methyl ester

Product 1

HCID 217063196-Hydroxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]-2-[4-[4-methoxy-4-oxobutoxy]phenyl]benzo[b]thiopheneYield 85.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

6-Benzyloxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]-2-[4-(4-methoxy-4-oxobutoxy)phenyl]benzo[b]thiophene (147 mg) in THF (3.0 mL) was treated sequentially with a solution of ammonium formate (25% in H2O, 2.0 mL) and 10% palladium on carbon (100 mg) at ambient temperature. The resulting mixture was stirred at ambient temperature under argon for 3 h before it was filtered through diatonaceous earth followed by rinsing with dichloromethane and methanol. The filtrate was extracted with dichloromethane (20 mL×3) from water (30 mL). The combined organic layers were dried with sodium sulfate and concentrated under reduced pressure. Chromatography with Et3N:EtOAc (0-5%) afforded the product (108 mg).

Workup

  1. filtrationwas filtered through diatonaceous earth
  2. washby rinsing with dichloromethane and methanol
  3. extractionThe filtrate was extracted with dichloromethane (20 mL×3) from water (30 mL)
  4. dry with materialThe combined organic layers were dried with sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dd22791eae894e5faa8c4e46093430e6
Source dataset
uspto-grants-2001_09
Patent number
US06284756B1

Reaction notes

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