Aluminium lithium hydride → HCID 66975707, compound

HRID 1022527Notes

Reaction equation

HRID 1022527 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:20][CH:19]([CH2:21][O:22][Si](C(C)(C)C)(C)C)[CH:18]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=2)[O:17]CC1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(NC[C@H]([C@@H](C1C=CC(Cl)=C(Cl)C=1)O)C(OC)=O)C1C=CC=CC=1>C1COCC1>[CH2:7]([NH:14][CH2:20][CH:19]([CH2:21][OH:22])[CH:18]([C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=1)[OH:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 66974911HCID 66974911, compoundHCID 66975969HCID 66975969, compound

Product 1

HCID 66975707HCID 66975707, compoundYield 119.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of lithium aluminum hydride (644 mg) in THF (40 mL) was added dropwise a solution of (6RS,7RS)-4-benzyl-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-7-(3,4-dichlorophenyl)-1,4-oxazepan-3-one (4.17 g) in THF (20 mL) under ice-cooling, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was cooled to −78° C., a solution of methyl (2R,3S)-2-[(benzylamino)methyl]-3-(3,4-dichlorophenyl)-3-hydroxypropanoate (10.8 g) in THF (80 mL) was added dropwise, and the mixture was stirred at 0° C. for 3 hr. The reaction mixture was poured into ice water, and the mixture was stirred for 30 min, and filtered through celite. The filtrate was extracted twice with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (3.44 g).

Workup

  1. temperaturecooling
  2. temperatureThe reaction mixture was cooled to −78° C.
  3. stirringthe mixture was stirred at 0° C. for 3 hr
  4. stirringthe mixture was stirred for 30 min
  5. filtrationfiltered through celite
  6. extractionThe filtrate was extracted twice with ethyl acetate
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c6460a84f07b4b45a81c906b681b77ae
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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