Sodium Hydroxide → HCID 22036736, compound

HRID 1789949Notes

Reaction equation

HRID 1789949 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][CH2:10][CH2:9][C:8](=O)[NH:7][C:6]=2[CH:13]=1.COCCO[AlH2-]OCCOC.[Na+].[OH-].[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][CH2:10][CH2:9][CH2:8][NH:7][C:6]=2[CH:13]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 16684438Red-AlHCID 22036759HCID 22036759, compound

Product 1

HCID 22036736HCID 22036736, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

7-fluoro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (76 mg, 0.38 mmol) dissolved in toluene (1 mL) and cooled to 0° C. in an ice bath. Red-Al (275 mL, 0.91 mmol) was added and then the reaction allowed to warm to room temperature. The reaction was heated at reflux for 1.5 hours. 1 N sodium hydoxide was added slowly until pH>10, this was stirred for 10 minutes, extracted with dichloromethane (3×25 mL), washed with water, and dried (sodium sulfate). The concentrated organics were purified by preparative thin layer chromatography on silica gel and eluted with 50% ethyl acetate in hexanes to give 7-fluoro-2,3,4,5-tetrahydro-1,5-benzothiazepine (30.8 mg, 93%). 1H NMR (CDCl3, 300 MHz): δ 7.32 (t, 1H, J=7.5 Hz), 6.53–6.42 (m, 2H), 4.09 (s-broad, 1H), 3.31–3.27 (m, 2H), 2.83–2.79 (m, 2H), 2.11–2.04 (m, 2H) ppm.

Workup

  1. temperatureto warm to room temperature
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 1.5 hours
  4. extractionextracted with dichloromethane (3×25 mL)
  5. washwashed with water
  6. dry with materialdried (sodium sulfate)
  7. customThe concentrated organics were purified by preparative thin layer chromatography on silica gel
  8. washeluted with 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-4072b995d7cd4225ad276ba347375802
Source dataset
uspto-grants-2006_07
Patent number
US07071186B2

Reaction notes

Loading…