Aluminium lithium hydride → HCID 57812432, compound

HRID 911998Notes

Reaction equation

HRID 911998 reaction equation
C[O:2][C:3]([C:5]1[C:9]2[CH:10]=[N:11][C:12]([NH2:26])=[C:13]([O:14][C@@H:15]([C:17]3[C:22]([Cl:23])=[CH:21][CH:20]=[C:19]([F:24])[C:18]=3[Cl:25])[CH3:16])[C:8]=2[O:7][CH:6]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:26][C:12]1[N:11]=[CH:10][C:9]2[C:5]([CH2:3][OH:2])=[CH:6][O:7][C:8]=2[C:13]=1[O:14][C@@H:15]([C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[C:19]([F:24])[C:18]=1[Cl:25])[CH3:16]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57812510HCID 57812510, compound

Product 1

HCID 57812432HCID 57812432, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-amino-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridine-3-carboxylic acid methyl ester (140 mg, 0.35 mmol) in THF (5 mL) was added 0.7 mL of LiAlH4 (1M solution in THF, 0.7 mmol) at 0° C. under nitrogen. The mixture was slowly warmed to rt. The reaction was quenched with EtOAc (25 mL), then water (1 mL). The organic phase was separated and washed with brine (10 mL), and dried over anhydrous sodium sulfate. The residue was purified by silica gel chromatography (Hex:EtOAc=50:50→100% EtOAc) to give the title compound as a white solid. LC-MS (ES+): 370.95/372.94 [MH+]. 1H NMR (CDCl3, 400 MHz): δ 1.66 (br s, 1H), 1.86 (d, J=6.6 Hz, 3H), 4.73 (br s, 2H), 4.79 (s, 2H), 6.53 (q, J=6.8 Hz, 1H), 7.04 (m, 1H), 7.27 (m, 1H), 7.37 (s, 1H), 8.10 (s, 1H).

Workup

  1. customThe reaction was quenched with EtOAc (25 mL)
  2. customThe organic phase was separated
  3. washwashed with brine (10 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe residue was purified by silica gel chromatography (Hex:EtOAc=50:50→100% EtOAc)

Sources & evidence

ORD record
ord-efb641aab027443fa59b205277866213
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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