Diisobutylaluminum hydride → HCID 86597139, compound

HRID 2373791Notes

Reaction equation

HRID 2373791 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C@@H:16]([NH:23][C:24]([C:26]3[CH:27]=[C:28]([C:34]4[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=4)[CH:29]=[CH:30][C:31]=3[O:32][CH3:33])=[O:25])[C:17](=[O:22])N(OC)C)=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].CC(C[AlH]CC(C)C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C@@H:16]([NH:23][C:24]([C:26]3[CH:27]=[C:28]([C:34]4[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:41])[F:42])=[CH:36][CH:35]=4)[CH:29]=[CH:30][C:31]=3[O:32][CH3:33])=[O:25])[CH:17]=[O:22])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 9855836Potassium sodium tartarateHCID 86597138HCID 86597138, compound

Product 1

HCID 86597139HCID 86597139, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

4-Methoxy-4′-trifluoromethyl-biphenyl-3-carboxylic acid [2-(3′-chloro-4′-fluoro-biphenyl-4-yl)-1-(R)-formyl-ethyl]-amide was synthesized by the following procedure: To 4-methoxy-4′-trifluoromethyl-biphenyl-3-carboxylic acid [2-(3′-chloro-4′-fluoro-biphenyl-4-yl)-1-(R)-(methoxy-methyl-carbamoyl)-ethyl]-amide (85 mg, 0.14 mmol) in THF (2 mL) was added DIBAL-H (0.64 mL, 0.64 mmol, 1.0 M in DCM) at −78° C. and the mixture was stirred at −78° C. for 2 h. After that potassium sodium tartrate was added and the mixture was stirred overnight, then the mixture was extracted with ethyl acetate (3×25 mL). Organic extracts were combined and concentrated in vacuo. The crude product was then purified with silica gel column chromatography by using ethyl acetate:hexanes (2:1) to afford the aldehyde intermediate(45 mg).

Workup

  1. stirringthe mixture was stirred overnight
  2. extractionthe mixture was extracted with ethyl acetate (3×25 mL)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was then purified with silica gel column chromatography

Sources & evidence

ORD record
ord-8b1465cb7abd469ea54e36551b770bb5
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Reaction notes

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