Tetrahydrofuran → HCID 67264474, compound

HRID 1687700Notes

Reaction equation

HRID 1687700 reaction equation
[N:1]([CH:4]1[C:10](=[O:11])[N:9]([CH2:12][CH3:13])[C:8]2[CH:14]=[CH:15][C:16]([N+:20]([O-:22])=[O:21])=[C:17]([O:18][CH3:19])[C:7]=2[CH2:6][CH2:5]1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCCC1>O>[NH2:1][CH:4]1[C:10](=[O:11])[N:9]([CH2:12][CH3:13])[C:8]2[CH:14]=[CH:15][C:16]([N+:20]([O-:22])=[O:21])=[C:17]([O:18][CH3:19])[C:7]=2[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 86634012HCID 86634012, compound

Product 1

HCID 67264474HCID 67264474, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combined (+/−)-3-Azido-1-ethyl-6-methoxy-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (280 mg), Triphenylphosphine Resin (1.0 mmol/g loading; 1.83 g), Tetrahydrofuran (25 mL) and Water (0.25 mL) and stir at rt overnight. Filter and concentrate. Strip down from benzene to remove water. (+/−)-3-Amino-1-ethyl-6-methoxy 7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one as an orangish oil isolated (251 mgs). 1H-NMR (CDCl3, 400 MHz): 7.84 (d, J=8.8 Hz, 1H), 7.10 (d, J=8.9 Hz, 1H), 4.36-4.28 (m, 1H), 3.97 (s, 3H), 3.71-3.62 (m, 1H), 3.36-3.31 (m, 1H), 3.23-3.18 (m, 1H), 2.52-2.39 (m, 2H), 2.03-1.99 (m, 1H), 1.66 (broad s, 2H), 1.21 (t, J=7.3 Hz, 3H). LC/MS: (M+H)+ found 280.18.

Workup

  1. filtrationFilter
  2. concentrationconcentrate
  3. customStrip down from benzene to remove water

Sources & evidence

ORD record
ord-3c17dfb7fd6d4d56b223d172e4959c17
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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