Carbonate Ion → HCID 67264126, compound

HRID 1040914Notes

Reaction equation

HRID 1040914 reaction equation
[CH3:1][O:2][C:3]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1.[F:17][C:18]([F:23])([F:22])[C@@H:19]1[CH2:21][O:20]1.C(=O)([O-])[O-]>C(#N)C>[F:17][C:18]([F:23])([F:22])[C@@H:19]([OH:20])[CH2:21][N:9]1[CH2:10][CH2:11][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:6]=2[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 19660Carbonate IonHCID 7171781(2S)-2-(Trifluoromethyl)oxiraneHCID 672643517-Methoxy-8-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 67264126HCID 67264126, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7-Methoxy-8-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (215 mg, 0.967 mmol) was placed into a sealable vial, suspended in Acetonitrile (10 mL) then (S)-2-Trifluoromethyl-oxirane (130 uL, 1.5 mmol) was added, followed by Macroporous carbonate resin (3.16 mmol/g loading; 0.810 g, 2.56 mmol). The reaction was stirred at room temperature for 24 h, filtered and concentrated in vacuo to afford (S)-1,1,1-Trifluoro-3-(7-methoxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-propan-2-ol as an orange oil (316 mg, 97%), which was used without further purification. 1H-NMR (CDCl3, 400 MHz) δ 7.67 (s, 1H), 6.83 (s, 1H), 4.05 (m, 1H), 3.95 (s, 3H), 2.6-3.0 (m, 10H); 19F-NMR (CDCl3, 376 MHz) δ −78.7 (s).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5207472f2eb94e98ac7d3ffed2982926
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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