Water → 4-[4-[6-Hydroxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]benzo[b]thiophen-2-yl]phenoxy]butanol Oxalate

HRID 1595051Notes

Reaction equation

HRID 1595051 reaction equation
C[O:2][C:3](=[O:46])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:18][C:17]3[CH:19]=[C:20]([O:23]CC4C=CC=CC=4)[CH:21]=[CH:22][C:16]=3[C:15]=2[CH2:31][C:32]2[CH:37]=[CH:36][C:35]([CH2:38][N:39]3[CH2:43][CH2:42][CH2:41][CH2:40]3)=[C:34]([O:44][CH3:45])[CH:33]=2)=[CH:10][CH:9]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH2:53].C1C[O:57]CC1>O.[OH-].[Na+]>[C:3]([OH:2])(=[O:46])[C:4]([OH:57])=[O:53].[OH:23][C:20]1[CH:21]=[CH:22][C:16]2[C:15]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([CH2:38][N:39]4[CH2:43][CH2:42][CH2:41][CH2:40]4)=[C:34]([O:44][CH3:45])[CH:33]=3)=[C:14]([C:11]3[CH:10]=[CH:9][C:8]([O:7][CH2:6][CH2:5][CH2:4][CH2:3][OH:2])=[CH:13][CH:12]=3)[S:18][C:17]=2[CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 217063264-[4-[6-Benzyloxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]benzo[b]thiophen-2-yl]phenoxy]butanoic acid methyl ester

Product 1

HCID 217063434-[4-[6-Hydroxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]benzo[b]thiophen-2-yl]phenoxy]butanol Oxalate

Reagents, catalysts & solvents 2

HCID 962WaterCatalyst2×HCID 14798Sodium HydroxideCatalyst

Procedure

The 4-[4-[6-benzyloxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]benzo[b]thiophen-2-yl]phenoxy]butanoic acid methyl ester prepared in Part A (91 mg; 0.14 mmol) was dissolved in anhydrous THF under argon atmosphere. LAH (10 mg; 0.29 mmol) was added. The mixture was stirred at room temperature for 3 h before it was hydrolyzed by addition of 2 drops of water, 2 drops of 5 M NaOH, and six drops of water. Additional water (25 mL) was added, and extraction was carried out with CH2Cl2. The combined organics were dried by passage through Na2SO4. Purification was effected by flash chromatography on silica gel, eluting with EtOAc(100-90%)/Et3N(0-5%)/MeOH(0-5%). The title product was obtained as a colorless oil (74 mg, 85%).

Workup

  1. extractionextraction
  2. dry with materialThe combined organics were dried by passage through Na2SO4
  3. customPurification
  4. washeluting with EtOAc(100-90%)/Et3N(0-5%)/MeOH(0-5%)

Sources & evidence

ORD record
ord-37a37e0a671e40ff927e7d7696fe31c2
Source dataset
uspto-grants-2001_09
Patent number
US06284756B1

Reaction notes

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