Toluene → HCID 68813248, compound

HRID 1296479Notes

Reaction equation

HRID 1296479 reaction equation
C([O:3][C:4]([C@@H:6]1[C@@H:12]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[CH2:11][CH:10]2[N:18]([CH3:19])[CH:7]1[CH2:8][CH2:9]2)=O)C.C1(C)C=CC=CC=1.COCCO[AlH2-]OCCOC.[Na+].[OH-].[Na+]>O>[CH3:19][N:18]1[CH:10]2[CH2:9][CH2:8][CH:7]1[C@H:6]([CH2:4][OH:3])[C@@H:12]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)[CH2:11]2

Participants

6

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 16684438Red-AlHCID 68810951HCID 68810951, compound

Product 1

HCID 68813248HCID 68813248, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of (2R,3S)-8-methyl-3-(2-thienyl)-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid ethyl ester (3.65 g, 13.75 mmol) and toluene (75 ml), Red-Al (6 ml, 65%, 20 mmol) was added at 0° C. The mixture was stirred at 0° C. for 1 h. A solution of aqueous sodium hydroxide (20 ml, 4 M) was added dropwise followed by warm water (50° C., 150 ml). The mixture was extracted with toluene (2×100 ml). The mixture was dried (MgSO4) and evaporated. The product was isolated as crystals. Mp: 153.7-157.5° C. Yield 2.04 g (63%).

Workup

  1. additionwas added at 0° C
  2. extractionThe mixture was extracted with toluene (2×100 ml)
  3. dry with materialThe mixture was dried (MgSO4)
  4. customevaporated
  5. customThe product was isolated as crystals

Sources & evidence

ORD record
ord-d89c7d615e5247309213fca1dd7ad8f4
Source dataset
uspto-grants-2007_07
Patent number
US07247643B2

Reaction notes

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