Lithium Chloride → HCID 57186048, compound

HRID 1003257Notes

Reaction equation

HRID 1003257 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:21][CH2:20][CH2:19][C@:10]2([O:14][CH2:13][C:12]([Sn](C)(C)C)=[CH:11]2)[C@@H:9]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[Li+].Br[C:31]1[CH:32]=[C:33]([O:46][CH3:47])[CH:34]=[CH:35][C:36]=1[N:37]1[C:41]([C:42]([F:45])([F:44])[F:43])=[N:40][N:39]=[N:38]1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:21][CH2:20][CH2:19][C@:10]2([O:14][CH2:13][C:12]([C:31]3[CH:32]=[C:33]([O:46][CH3:47])[CH:34]=[CH:35][C:36]=3[N:37]3[C:41]([C:42]([F:43])([F:44])[F:45])=[N:40][N:39]=[N:38]3)=[CH:11]2)[C@@H:9]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 433294Lithium ChlorideHCID 10885282HCID 10885282, compoundHCID 18796385HCID 18796385, compound

Product 1

HCID 57186048HCID 57186048, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of (5R,6S)-7-(tert-butoxycarbonyl)-6-phenyl-3-(trimethylstannyl)-7-aza-1-oxa-spiro[4.5]dec-3-ene (0.5 g, 1 mmol; Desc.6), lithium chloride (0.266 g, 6 mmol) and 3-bromo-4-(5-(trifluoromethyl)-tetrazol-1-yl)anisole (0.404 g, 1.2 mmol; Desc. 7c) in toluene (15 ml) was degassed and purged with nitrogen before addition of tetrakis(triphenylphosphine)palladium(0) (0.06 g). The mixture was degassed thoroughly, and the solution was heated to 110° C. for 19 hours. The solvent was evaporated in vacuo. The residue was dry loaded onto silica from methanol, and purified by chromatography on silica eluting with 10-20% ethyl acetate in hexane, to afford the title compound as a yellow oil (500 mg, 90%) MS (CI+) m/z 558 (M+H, 60%). 1H NMR (250 MHz, CDCl3) δ 1.34 (9H, s), 1.50 (1H, m), 1.55 (1H, m), 1.67 (1H, m), 1.87 (1H, m), 3.08 (1H, m), 3.88 (3H, s), 4.02 (1H, m), 4.30 (1H, dd, J 2.1 Hz, J 12.4 Hz), 4.46 (1H, dd, J 2.1 Hz, J 12.4 Hz), 4.92 (1H, s), 5.30 (1H, t, J 0.9 Hz), 6.68 (1H, d, J 2.8 Hz), 6.98 (1H, dd, J 2.8 Hz, J 8.8 Hz), 7.25 (6H, m).

Workup

  1. customwas degassed
  2. custompurged with nitrogen before addition of tetrakis(triphenylphosphine)palladium(0) (0.06 g)
  3. customThe mixture was degassed thoroughly
  4. customThe solvent was evaporated in vacuo
  5. customThe residue was dry
  6. custompurified by chromatography on silica eluting with 10-20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1ad3bc9376ba4e719bf91c59a18cbb0c
Source dataset
uspto-grants-2000_04
Patent number
US06046195

Reaction notes

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