Potassium sodium tartarate → 3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-chloro-benzylamine

HRID 2428097Notes

Reaction equation

HRID 2428097 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([SiH2:11][O:12][C:13]([CH3:25])([CH3:24])[C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH:17]=[N:18]O)([CH3:10])([CH3:9])[CH3:8].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>CCOCC>[C:7]([SiH2:11][O:12][C:13]([CH3:25])([CH3:24])[C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:17][NH2:18])([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 1373299193-(tert-Butyl-dimethyl-silanyloxymethyl)-4-chloro-benzaldehyde oxime

Product 1

HCID 1373299203-(tert-Butyl-dimethyl-silanyloxymethyl)-4-chloro-benzylamineYield 99.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

LiAlH4 (4.11 g, 108 mmol) was added in portions to a sol. of 3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-benzaldehyde oxime (13.0 g, 43.4 mmol) in Et2O (433 mL). The mixture was stirred for 1 h at rt. Aq. sat. potassium sodium tartrate (400 mL) was carefully added to the mixture. The mixture was stirred for 3 h, and was extracted with Et2O (3×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying under high vacuum yielded the crude title compound (12.4 g, quantitative yield) that was used further without purification. LC-MS: tR=0.84 min; ES+: 327.37.

Workup

  1. stirringThe mixture was stirred for 3 h
  2. extractionwas extracted with Et2O (3×)
  3. dry with materialextracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customDrying under high vacuum

Sources & evidence

ORD record
ord-2ee0c7d1a76f4834abd25aece9093446
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

Loading…