1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 59432483, compound

HRID 507055Notes

Reaction equation

HRID 507055 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C@@H:11](O)[C:10]2[CH:16]=[C:17]([CH2:24][CH3:25])[C:18]([C:20]([F:23])([F:22])[F:21])=[CH:19][C:9]1=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P([N:40]=[N+:41]=[N-:42])(C2C=CC=CC=2)=O)C=CC=CC=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C@H:11]([N:40]=[N+:41]=[N-:42])[C:10]2[CH:16]=[C:17]([CH2:24][CH3:25])[C:18]([C:20]([F:23])([F:22])[F:21])=[CH:19][C:9]1=2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 59432328HCID 59432328, compound

Product 1

HCID 59432483HCID 59432483, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Heat a mixture of (R)-7-ethyl-5-hydroxy-8-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid tert-butyl ester (7.59 g, 21.12 mmol), diphenylphosphoryl azide (DPPA, 5.50 mL, 25.64 mmol) and DBU (3.95 mL, 26.41 mmol) in toluene (200 mL) at 65° C. under nitrogen for 12 h. Add silica gel to the cooled mixture and remove the solvents under reduced pressure. Purify the residue by column chromatography, eluting with ethyl acetate/hexanes (1:2), to provide the title compound as a colorless oil (5.79 g, 71%): 1H NMR (CDCl3, 300 MHz) δ 1.21-2.30 (m, 18H), 2.83-2.89 (m, 2H), 4.78-4.80 (m, 1H), 7.31-7.45 (m, 2H); APCI MS m/z 356 (M−N2)−.

Workup

  1. temperatureHeat
  2. customAdd silica gel to the cooled mixture and remove the solvents under reduced pressure
  3. customPurify the residue by column chromatography
  4. washeluting with ethyl acetate/hexanes (1:2)

Sources & evidence

ORD record
ord-fc7f308a1a2a467dbef7c39140eebd75
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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