Methanol → HCID 58415344, compound

HRID 2075164Notes

Reaction equation

HRID 2075164 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16]([C:18]#[N:19])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N:24]=[N+:25]=[N-:26])(C)C.C([Sn](=O)CCCC)CCC.CO>C1(C)C=CC=CC=1.ClCCl>[CH:1]([N:14]1[CH2:17][CH:16]([C:18]2[N:24]=[N:25][NH:26][N:19]=2)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 27792901-(Diphenylmethyl)azetidine-3-carbonitrile

Product 1

HCID 58415344HCID 58415344, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

1-Benzhydrylazetidine-3-carbonitrile (2.48 g, 10 mmol), trimethylsilyl azide (2.30 g, 20 mmol) and dibutyltin oxide (498 mg, 2.0 mmol) were dissolved in toluene (20 mL) and heated to reflux for 32 h. The reaction mixture was then cooled to room temperature and applied directly to ISCO system with 10% methanol in dichloromethane to give the product. 1H NMR (400 MHz, CDCl3) δ 7.54 (m, 4H), 7.31 (m, 6H), 5.11 (s, 1H), 4.47 (m, 1H), 4.05 (t, J=7.2 Hz, 2H), 3.91 (t, J=7.2 Hz, 2H). MS (ESI) m/z: Calculated: 291.15; Observed: 291.90 (M++1).

Workup

  1. temperatureheated
  2. temperatureto reflux for 32 h
  3. customto give the product

Sources & evidence

ORD record
ord-78b419a29c4d4dddac3133ea652c29fc
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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