Tetrahydrofuran → HCID 66616500, compound

HRID 1889686Notes

Reaction equation

HRID 1889686 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][NH:7][C:8](=O)[C:9]2[C:10](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=O)=[CH:4][CH:3]=1.C1COCC1>CO>[C:9]1([CH2:8][NH:7][CH2:6][C:5]2[CH:27]=[CH:28][C:2]([F:1])=[CH:3][CH:4]=2)[CH:25]=[CH:24][CH:23]=[CH:22][C:10]=1[CH2:11][NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 1000719HCID 1000719, compound

Product 1

HCID 66616500HCID 66616500, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a 500 mL 3-neck round bottom flask fitted with condenser and nitrogen tube, was added N1,N2-bis(4-fluorobenzyl)phthalamide (2 g, 5.2 mmol, 1 eq) and THF (HPLC grade 100 mL). The clear solution was cooled to 0° C., before borondimethylsulphide (12 g, 15 mL, 164 mmol, 30 eq) was added slowly. The reaction mixture refluxed for 36 h, cooled to −10° C. to −15° C. and treated with methanol slowly through a dropping funnel until frothing stopped (50 mL). The reaction mixture concentrated to dryness and once again cooled to 0° C., before methanol (100 mL) was added slowly, The reaction mixture was refluxed for 40 h and concentrated under vacuum to dryness to give the crude product (1.5 g, 85%) as a solid, which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 7.32-7.28 (m 6H), 7.22-7.19 (m, 2H), 7.10-7.05 (m, 4H), 3.72-3.64 (m, 8H). MS (ESI): 353.2 (M+H)+.

Workup

  1. customTo a 500 mL 3-neck round bottom flask fitted with condenser and nitrogen tube
  2. additionwas added slowly
  3. temperatureThe reaction mixture refluxed for 36 h
  4. temperaturecooled to −10° C. to −15° C.
  5. concentrationThe reaction mixture concentrated to dryness
  6. temperatureonce again cooled to 0° C., before methanol (100 mL)
  7. additionwas added slowly
  8. temperatureThe reaction mixture was refluxed for 40 h
  9. concentrationconcentrated under vacuum to dryness

Sources & evidence

ORD record
ord-cf38378b7e0c4149b9c854f88081c0b3
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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