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Dichloromethane → 3-(Tert-butyldimethylsilyloxy)-1-(3,4-difluorophenyl)propan-1-amine

HRID 2279542
Notes
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Reaction equation

HRID 2279542 reaction equation
[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([F:13])[CH:7]=1)[CH2:3][CH2:4][OH:5].[CH3:14][C:15]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])[CH3:16].CCN(C(C)C)C(C)C.C(Cl)Cl>CN(C1C=CN=CC=1)C.O>[Si:18]([O:5][CH2:4][CH2:3][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([F:13])[CH:7]=1)[NH2:1])([C:15]([CH3:17])([CH3:16])[CH3:14])([CH3:20])[CH3:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 623897353-Amino-3-(3,4-difluorophenyl)propan-1-ol

Product 1

HCID 682943123-(Tert-butyldimethylsilyloxy)-1-(3,4-difluorophenyl)propan-1-amineYield 69.9%

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 962WaterSolvent

Procedure

A solution of 304 (0.400 g, 2.14 mmol), TBDMS-Cl (0.386 g, 2.56 mmol), DIPEA (0.744 mL, 4.27 mmol), DMAP (0.0261 g, 0.214 mmol) and DCM (10 mL) was stirred at RT for 1 h and then poured into water and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (500:7) to afford 0.45 g (69.9%) of 3-(tert-butyldimethylsilyloxy)-1-(3,4-difluorophenyl)propan-1-amine (306).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by SiO2 chromatography
  6. washeluting with DCM/MeOH (500:7)

Sources & evidence

ORD record
ord-f64a70a54dfb425a98a88cc59d9d4b4e
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