6-cyano-7-fluoro-3,4-dihydro-2H-chromene-4-carboxylic acid → Tert-butyl 6-cyano-7-fluorochroman-4-carboxylate

HRID 1626387Notes

Reaction equation

HRID 1626387 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[F:13])[O:9][CH2:8][CH2:7][CH:6]2[C:14]([OH:16])=[O:15])#[N:2].C(N/C(=N/C(C)C)/O[C:23]([CH3:26])([CH3:25])[CH3:24])(C)C>C1COCC1.CCOCC>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[F:13])[O:9][CH2:8][CH2:7][CH:6]2[C:14]([O:16][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:15])#[N:2]

Participants

5

Reactant 2

HCID 670802696-cyano-7-fluoro-3,4-dihydro-2H-chromene-4-carboxylic acidHCID 178457538HCID 178457538, compound2×

Product 1

HCID 67288243Tert-butyl 6-cyano-7-fluorochroman-4-carboxylateYield 64%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

6-Cyano-7-fluoro-3,4-dihydro-2H-chromene-4-carboxylic acid was dissolved in 10 mL of THF and treated with (Z)-tert-butyl N,N′-diisopropylcarbamimidate. After stirring for 3 hours, an additional 2 mL of (Z)-tert-butyl N,N′-diisopropylcarbamimidate was added and the reaction was stirred overnight. The reaction was diluted with ether, filtered, concentrated onto silica gel and flashed with 8:1 hexanes/ethyl acetate to provide the desired product (1.4 g, 64% yield) as a white solid.

Workup

  1. stirringthe reaction was stirred overnight
  2. filtrationfiltered
  3. concentrationconcentrated onto silica gel

Sources & evidence

ORD record
ord-4f8b8acdcf384bc58f8f916559ef46c0
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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