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Dichloromethane → 3-(Tert-butyldimethylsilyloxy)-1-(3-fluoro-4-(trifluoromethyl)phenyl)propan-1-amine

HRID 2279530
Notes
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Reaction equation

HRID 2279530 reaction equation
[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[C:8]([F:16])[CH:7]=1)[CH2:3][CH2:4][OH:5].[CH3:17][C:18]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])[CH3:19].CCN(C(C)C)C(C)C.C(Cl)Cl>CN(C1C=CN=CC=1)C.O>[Si:21]([O:5][CH2:4][CH2:3][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:13])([F:14])[F:15])=[C:8]([F:16])[CH:7]=1)[NH2:1])([C:18]([CH3:20])([CH3:19])[CH3:17])([CH3:23])[CH3:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 682943283-Amino-3-(3-fluoro-4-(trifluoromethyl)phenyl)propan-1-ol

Product 1

HCID 867055273-(Tert-butyldimethylsilyloxy)-1-(3-fluoro-4-(trifluoromethyl)phenyl)propan-1-amineYield 70.9%

Reagents, catalysts & solvents

2
HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

solution of 276 (0.200 g, 0.843 mmol), TBDMS-Cl (0.153 g, 1.01 mmol), DIPEA (0.294 mL, 1.69 mmol), DMAP (0.0103 g, 0.0843 mmol) and DCM (6 mL) was stirred for 1 h at RT and then poured into H2O, and extracted with DCM. The combined organic fractions were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (500:5) to afford 0.210 g (70.9%) of 3-(tert-butyldimethylsilyloxy)-1-(3-fluoro-4-(trifluoromethyl)phenyl)propan-1-amine (278).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic fractions were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by SiO2 chromatography
  6. washeluting with DCM/MeOH (500:5)

Sources & evidence

ORD record
ord-3f6ba1f9122d444a8329c5dfd35ca589
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09133187B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes