Toluene → HCID 69663212, compound

HRID 2212088Notes

Reaction equation

HRID 2212088 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.Cl.C[O:20][C:21](=O)[C:22]([S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:37])=[O:36])([CH3:34])[CH2:23][CH2:24][CH2:25][N:26]1[CH2:31][C:30]([CH3:32])=[C:29]([CH3:33])[CH2:28][CH2:27]1>ClCCl>[C:38]1([S:35]([C:22]([CH3:34])([CH2:23][CH2:24][CH2:25][N:26]2[CH2:31][C:30]([CH3:32])=[C:29]([CH3:33])[CH2:28][CH2:27]2)[CH2:21][OH:20])(=[O:36])=[O:37])[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 21225700DiisobutylaluminumhydrideHCID 69663074HCID 69663074, compound

Product 1

HCID 69663212HCID 69663212, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of diisobutylaluminium hydride in toluene (1.0M, 6 ml, 0.6 mmol) was added to a stirred solution of 2-benzenesulfonyl-5-(4,5-dimethyl-3,6-dihydro-2H-pyridin-1-yl)-2-methyl-pentanoic acid methyl ester hydrochloride (60 mg, 0.15 mmol) in dichloromethane at 5° C. The mixture was stirred for 30 min., diluted with dichloromethane (15 ml) and quenched with water (3 drops). The resulting mixture was stirred for 30 min. and solid Na2SO4 was added. The mixture was filtered through a pad of Celite and concentrated. The residue was purified on silica gel (dichloromethane:methanol) to give the title product.

Workup

  1. customquenched with water (3 drops)
  2. stirringThe resulting mixture was stirred for 30 min.
  3. additionsolid Na2SO4 was added
  4. filtrationThe mixture was filtered through a pad of Celite
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel (dichloromethane:methanol)

Sources & evidence

ORD record
ord-7f7cf7a34de3405a9b88e45bf6e060c8
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

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