Tetrahydrofuran → HCID 67459966, compound

HRID 625066Notes

Reaction equation

HRID 625066 reaction equation
[CH3:1][CH2:2][Mg+].[Br-].C1COCC1.[Si:10]([O:17][CH2:18][CH:19]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[C:20]#[N:21])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].[OH-].[Na+]>CCOCC.C(Cl)Cl>[Si:10]([O:17][CH2:18][CH:19]([C:20]1([NH2:21])[CH2:2][CH2:1]1)[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 67457927HCID 67457927, compoundHCID 178461630HCID 178461630, compound

Product 1

HCID 67459966HCID 67459966, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of EtMgBr in THF (3.0M, 8.0 mL, 24 mmol) was added dropwise at room temperature to a stirred solution of 3-(tert-butyldimethylsilyloxy)-2-(4-chlorobenzyl)propanenitrile (3.7 g, 12 mmol) and Ti(i-PrO)4 (3.9 mL, 13 mmol) in Et2O (50 mL). After the mixture was stirred at room temperature for 1 hour, BF3OEt (3.0 mL, 24 mmol) was added at once. The mixture was stirred for an additional 1 hour. A solution of 10% NaOH (10 mL) was added, followed by DCM (300 mL). The resulting precipitate was filtered and washed with DCM. The combined filtrates were dried and concentrated. The residue was purified by column chromatography (30:1 DCM:MeOH) to give 1-(1-(tert-butyldimethylsilyloxy)-3-(4-chlorophenyl)propan-2-yl)cyclopropanamine (2.6 g, 64%) as a colorless oil. LCMS: 340.2 (M+H)+ (APCI+); Rf: 3.17 min.

Workup

  1. additionBF3OEt (3.0 mL, 24 mmol) was added at once
  2. stirringThe mixture was stirred for an additional 1 hour
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with DCM
  5. customThe combined filtrates were dried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (30:1 DCM:MeOH)

Sources & evidence

ORD record
ord-8d31270a49164a08a6d3636af8a212e1
Source dataset
uspto-grants-2016_04
Patent number
US09303040B2

Reaction notes

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