Aluminium lithium hydride → HCID 54450846, compound

HRID 1387098Notes

Reaction equation

HRID 1387098 reaction equation
C[O:2][C:3](=O)[C@H:4]([CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:18][C:17]3[CH:19]=[C:20]([OH:23])[CH:21]=[CH:22][C:16]=3[C:15]=2[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)=[C:27]([O:37][CH3:38])[CH:26]=2)=[CH:10][CH:9]=1)[NH2:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.C(Cl)Cl>[NH2:5][C@H:4]([CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:18][C:17]3[CH:19]=[C:20]([OH:23])[CH:21]=[CH:22][C:16]=3[C:15]=2[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][N:32]3[CH2:33][CH2:34][CH2:35][CH2:36]3)=[C:27]([O:37][CH3:38])[CH:26]=2)=[CH:10][CH:9]=1)[CH2:3][OH:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 70094128HCID 70094128, compound

Product 1

HCID 54450846HCID 54450846, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

O-[4-[6-Hydroxy-3-[3-methoxy-4-[(1-pyrrolidinyl)methyl]benzyl]benzo[b]thiophen-2-yl]phenyl]-L-serine methyl ester (25 mg, 0.045 mmol) in THF:CH2Cl2 (3:1, 4 mL) was treated with lithium aluminum hydride (12 mg) at ambient temperature under argon for 3 h. The reaction was quenched with water (0.5 mL) and sodium hydroxide solution (1.0 M, 1 mL) and stirred for 30 more min before dilution with water (50 mL) and extracting with ethyl acetate (50 mL×3). The combined organic layers were dried with sodium sulfate and concentrated under reduced pressure. Preparative thin layer chromatography with Et3N:MeOH:EtOAc (10:20:70) afforded the product as a white solid (8 mg, 34%).

Workup

  1. customThe reaction was quenched with water (0.5 mL) and sodium hydroxide solution (1.0 M, 1 mL)
  2. extractionextracting with ethyl acetate (50 mL×3)
  3. dry with materialThe combined organic layers were dried with sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9f857c4540f846b19bb8c207346d46fd
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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