Diisobutylaluminumhydride → HCID 69469996, compound

HRID 853783Notes

Reaction equation

HRID 853783 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:9][CH2:8][C@@H:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[N:6]1[S:17]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)(=[O:19])=[O:18])=O.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([S:17]([N:6]2[C@H:7]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=3)[CH2:8][CH2:9][C@@H:5]2[CH2:3][OH:2])(=[O:18])=[O:19])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 69474915HCID 69474915, compound

Product 1

HCID 69469996HCID 69469996, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (2R,5S)-1-(4-chloro-benzenesulfonyl)-5-(3-fluoro-phenyl)-pyrrolidine-2-carboxylic acid methyl ester (0.45 g, 1.1 mmol) in anhydrous toluene (5 mL) at 0° C. was added dropwise diisobutylaluminum hydride (1M in hexane, 6.4 mL, 6.4 mmol). The mixture was allowed to warm to room temperature and stirred for 16 hr. The reaction was quenched by adding 1 N HCl (10 mL) and the mixture diluted with EtOAc (20 mL). The organic phase was separated, washed with 10% NaHCO3 and brine, dried (Na2SO4) and concentrated under vacuum to give 0.40 g (99%) of (2R,5S)-[1-(4-chloro-benzenesulfonyl)-5-(3-fluoro-phenyl)-pyrrolidin-2-yl]-methanol as a yellowish solid. 1H NMR (CDCl3, 300 MHz) δ 7.89 (2H, d), 7.62 (2H, d), 7.50–7.20 (3H, m), 7.06 (1H, td), 4.84 (1H, t), 4.05–3.85 (3H, m), 2.05 (2H, q), 1.95–1.80 (3H, m). The 1H NMR spectrum showed complete conversion of ester to alcohol and the material was used without further purification.

Workup

  1. customThe reaction was quenched
  2. additionby adding 1 N HCl (10 mL)
  3. additionthe mixture diluted with EtOAc (20 mL)
  4. customThe organic phase was separated
  5. washwashed with 10% NaHCO3 and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-09ed9a24eafe4b4cba75d32161c509c2
Source dataset
uspto-grants-2007_08
Patent number
US07256186B2

Reaction notes

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