tert-Butyldimethylsilyl trifluoromethanesulphonate → HCID 131733485, compound

HRID 2279523Notes

Reaction equation

HRID 2279523 reaction equation
Cl.[NH2:2][C@@H:3]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1)[C@H:4]([OH:7])[CH2:5][OH:6].[Si:16](OS(C(F)(F)F)(=O)=O)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Si:16]([O:7][C@H:4]([CH2:5][O:6][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[C@H:3]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1)[NH2:2])([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 516892Sodium BicarbonateHCID 86705521HCID 86705521, compound

Product 1

HCID 131733485HCID 131733485, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 252 (0.50 g, 1.83 mmol) and DCM (5 mL) at RT was added TEA (1.28 mL, 9.17 mmol) followed by TBDMSOTf (1.05 mL, 4.59 mmol) and the reaction was stirred for 30 min. The reaction poured into aq. NaHCO3 and extracted with DCM. The combined extracts were dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with hexane/EtOAc/DCM (8:1:1) to afford 0.280 g (32.9%) of (1S,2S)-2,3-bis-(tert-butyldimethylsilyloxy)-1-(3,4-dichlorophenyl)propan-1-amine (254).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by SiO2 chromatography
  6. washeluting with hexane/EtOAc/DCM (8:1:1)

Sources & evidence

ORD record
ord-c031c39a15924523812986efec176bd2
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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