Aluminium lithium hydride → HCID 67180539, compound

HRID 1807950Notes

Reaction equation

HRID 1807950 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]([C@@H:10]([CH2:20][O:21][C:22]([C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)([CH3:24])[CH3:23])[CH2:11][O:12][Si](C(C)(C)C)(C)C)=[N+]=[N-]>O1CCCC1>[NH2:7][C@@H:10]([CH2:20][O:21][C:22]([C:25]1[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=1)([CH3:24])[CH3:23])[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86638537HCID 86638537, compound

Product 1

HCID 67180539HCID 67180539, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of lithiumaluminiumhydride (41 mg) in dry tetrahydrofuran (2 ml) was added dropwise under an argon atmosphere a solution of {(S)-2-azido-3-[1-(4-fluorophenyl)-1-methyl-ethoxy]-propoxy}-tert-butyl-dimethyl-silane (200 mg) in dry tetrahydrofuran (0.5 ml). The reaction mixture was stirred at room temperature for 48 hours and quenched by addition of water (0.04 ml), NaOH 4 N (0.04 ml) and H2O (0.12 ml). The suspension was stirred for 30 min and was filtered through Celite and MgSO4. The filtrate was evaporated to give crude (R)-2-amino-3-[1-(4-fluoro-phenyl)-1-methyl-ethoxy]-propan-1-ol (128 mg) as a light yellow liquid. MS (ISP): 228.3 ([M+H]+)

Workup

  1. customquenched by addition of water (0.04 ml), NaOH 4 N (0.04 ml) and H2O (0.12 ml)
  2. stirringThe suspension was stirred for 30 min
  3. filtrationwas filtered through Celite and MgSO4
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-4faf362516f147bd8471b290b3121513
Source dataset
uspto-grants-2013_01
Patent number
US08357712B2

Reaction notes

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