Dichloromethane → HCID 68294425, compound

HRID 2279495Notes

Reaction equation

HRID 2279495 reaction equation
[NH2:1][C@@H:2]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([Cl:13])[CH:7]=1)[CH2:3][CH2:4][OH:5].C(Cl)Cl.[CH3:17][C:18]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C1C=CN=CC=1)C.O>[Si:21]([O:5][CH2:4][CH2:3][C@H:2]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([Cl:13])[CH:7]=1)[NH2:1])([C:18]([CH3:20])([CH3:19])[CH3:17])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 6344Dichloromethane2×HCID 28928tert-Butyldimethylsilyl chlorideHCID 40425511HCID 40425511, compound

Product 1

HCID 68294425HCID 68294425, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

A round-bottom flask was charged with (R)-3-amino-3-(3,4-dichlorophenyl)propan-1-ol (9.25 g, 42.0 mmol, CASRN 147611-61-8), DMAP (0.513 g, 4.20 mmol) and DCM (84.1 mL) then a solution of TBDMS-Cl (6.65 g, 44.1 mmol) and DCM (10 mL) was added. The reaction was stirred at RT for 2 d. The reaction mixture was poured into water and extracted with DCM. The organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with a DCM/MeOH gradient (500:8 to 500:10) to afford 10.2 g (72%) of (R)-3-(tert-butyl dimethylsilyloxy)-1-(3,4-dichlorophenyl)propan-1-amine (186): m/z (APCI-pos) M+1=334.0.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by SiO2 chromatography
  6. washeluting with a DCM/MeOH gradient (500:8 to 500:10)

Sources & evidence

ORD record
ord-6607d8c208ed4e2cadf5f02a85f1ba95
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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