Methanol → [2-Phenyl-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrol-3-yl]-methanol

HRID 1295355Notes

Reaction equation

HRID 1295355 reaction equation
C([O:3][C:4]([C:6]12C[CH:10]1[CH2:9][N:8]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:7]2[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=O)C.C(OC(C1[C@H](C2C=CC=CC=2)N(S(C2C=CC(C)=CC=2)(=O)=O)CC=1)=O)C.CC(C[AlH]CC(C)C)C.CO>C(Cl)Cl>[C:22]1([CH:7]2[C:6]([CH2:4][OH:3])=[CH:10][CH2:9][N:8]2[S:12]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)(=[O:14])=[O:13])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14487Diisobutylaluminum hydrideHCID 589073302-Phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carboxylic acid ethyl esterHCID 69337074(S)-2-phenyl-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester

Product 1

HCID 58907347[2-Phenyl-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrol-3-yl]-methanolYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-25 °C

Procedure

To racemic intermediate 1, one enantiomer being (S)-2-phenyl-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester (1.8 g, 5.0 mmol), was dissolved in methylene chloride (60 mL) in a three necked flask equipped with an addition funnel and an internal thermometer. The mixture was cooled to −25° C., DIBAL (1M/toluene, 12.5 mL, 12.5 mmol) was added dropwise and the reaction stirred for an additional 0.5 hours. Methanol was added to the cold solution until gas evolution ceased and the solvents were then removed at reduced pressure. The residue was partitioned between a saturated solution of Rochelle's salt and methylene chloride. The organics were washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude product was chromatographed on silica gel using a gradient of 20% to 60% ETOAc/Hexanes to yield the title compound as a sticky foam (1.6 g, 98% yield).

Workup

  1. customequipped with an addition funnel
  2. customthe solvents were then removed at reduced pressure
  3. customThe residue was partitioned between a saturated solution of Rochelle's salt and methylene chloride
  4. washThe organics were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was chromatographed on silica gel using a gradient of 20% to 60% ETOAc/Hexanes

Sources & evidence

ORD record
ord-f781173d1846437ebbdbf294fb1807d2
Source dataset
uspto-grants-2007_07
Patent number
US07241798B2

Reaction notes

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