Water → HCID 22620711, compound

HRID 841024Notes

Reaction equation

HRID 841024 reaction equation
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:15]=[CH:14][C:7]2[NH:8][C:9](=O)[CH2:10][CH2:11][S:12][C:6]=2[CH:5]=1.[AlH4-].[Li+].O.[Cl-].[Na+]>O1CCCC1.C(OCC)(=O)C>[F:17][C:2]([F:1])([F:16])[O:3][C:4]1[CH:15]=[CH:14][C:7]2[NH:8][CH2:9][CH2:10][CH2:11][S:12][C:6]=2[CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 28112Lithium aluminum hydrideHCID 22620691HCID 22620691, compound

Product 1

HCID 22620711HCID 22620711, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

8-Trifluoromethoxy-2,3,4,5-tetrahydro-[1,5]-enzothiazepine may be prepared in the following manner: a solution of 2.5 g of 8-trifluoromethoxy-2,3-dihydro-5H-[1,5]benzothiazepin-4-one in 25 ml of tetrahydrofuran is added dropwise over 15 minutes to 21.4 ml of an approximately 0.5 M solution of lithium tetrahydroaluminate in tetrahydrofuran, kept under argon at 5° C. The reaction mixture is then stirred for 2 hours at 20° C. and 500 ml of distilled water, 100 ml of ethyl acetate and 100 ml of a saturated sodium chloride solution are added successively. After decantation, the aqueous phase is extracted three times with 50 ml of ethyl acetate. The organic extracts are combined, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2 kPa). 2 g of 8-trifluoromethoxy-2,3,4,5-tetrahydro-[1,5]benzothiazepine are thus obtained in the form of a yellow oil [1H NMR spectrum in DMSO-d6, T=300K, δin ppm (300 Mhz): 1.95 (2H, m, CH2); 3.00 (2H, m, SCH2); 3.30 (2H, m, NCH2); 5.90 (1H, m, NH); 6.85 (1H, d, J=8 Hz, arom. CH); 7.00 (1H, d, J=8Hz, arom. CH); 7.12 (1H, s, arom. CH)].

Workup

  1. custom8-Trifluoromethoxy-2,3,4,5-tetrahydro-[1,5]-enzothiazepine may be prepared in the following manner
  2. customkept under argon at 5° C
  3. extractionAfter decantation, the aqueous phase is extracted three times with 50 ml of ethyl acetate
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated to dryness under reduced pressure (2 kPa)

Sources & evidence

ORD record
ord-3fdb1dfd4eb24a12bfdb0c47f42d555c
Source dataset
uspto-grants-2002_04
Patent number
US06369221B1

Reaction notes

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