Sodium Hydroxide → HCID 66975115, compound

HRID 1022545Notes

Reaction equation

HRID 1022545 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:11]([N:18]1[CH2:24][CH:23]([CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH:22]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([Cl:41])[CH:35]=2)[O:21][CH2:20][C:19]1=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+]>C(OCC)C.C1COCC1>[CH2:11]([N:18]1[CH2:24][CH:23]([CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH:22]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([Cl:41])[CH:35]=2)[O:21][CH2:20][CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 66974911HCID 66974911, compound

Product 1

HCID 66975115HCID 66975115, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of lithium aluminum hydride (1.49 g) in diethyl ether (120 mL) was added, under a nitrogen stream, aluminum(III) chloride (1.74 g) under ice-cooling, and the mixture was stirred at room temperature for 40 min. The reaction mixture was cooled to −78° C., a solution of (6RS,7SR)-4-benzyl-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-7-(3,4-dichlorophenyl)-1,4-oxazepan-3-one (10.8 g) in THF (80 mL) was added dropwise, and the mixture was stirred at 0° C. for 3 hr. To the reaction mixture was added 1 N aqueous sodium hydroxide solution (22 mL) at −78° C., and the mixture was stirred at room temperature for 2 hr, and filtered through celite. The filtrate was concentrated under reduced pressure to give the title compound (9.77 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 at room temperature for 2 hr
  5. filtrationfiltered through celite
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2293c8d4f79b4fab9439756951da827b
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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