Potassium Sodium Tartrate → HCID 16733885, compound

HRID 1877327Notes

Reaction equation

HRID 1877327 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=O)=[CH:4][CH:3]=1.[NH2:13][C:14]1[S:15][CH2:16][CH2:17][N:18]=1.[BH4-].[Na+].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][CH:9]2[NH:13][C:14]2[S:15][CH2:16][CH2:17][N:18]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 9357Potassium Sodium TartrateHCID 156894,5-Dihydro-2-thiazolamineHCID 2566777-Chloro-1,2,3,4-tetrahydronaphthalen-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 16733885HCID 16733885, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Procedure

Titanium isopropoxide (710 mg, 0.74 mls, 2.5 mmol) is added to a mixture of 7-chloro-1-tetralone (360 mg, 2 mmol) and 2-aminothiazoline (224 mg, 2.2 mmol). The reaction mixture is stirred for 16 hours at room temperature, then diluted with dry methanol (5 ml). Excess sodium borohydride is added carefully portionwise over a period of 45 minutes. The reaction mixture is stirred for a further 2 hours, then added to a saturated aqueous solution of Rochelle's salt and extracted with dichloromethane (2×25 mls). The organic phases are combined, washed sequentially with water and saturated brine, then filtered through a pad of magnesium sulphate. The filtrate is concentrated under reduced pressure to give the crude product as a pale yellow gum. The crude product is purified by column chromatography on silica, eluting with ethyl acetate to give the title compound as a white solid Mp 164-6° C. Nmr data: (CDCl3): 7.39 (1H, s, CH), 7.13 (1H, dd, CH), 7.01 (1H, s, CH), 4.90 (1H, m, CH), 4.06 (2H, m), 3.37 (2H, m), 2.72 (2H, m), 2.08 (1H, m), 1.85 (3H, m)

Workup

  1. stirringThe reaction mixture is stirred for a further 2 hours
  2. extractionextracted with dichloromethane (2×25 mls)
  3. washwashed sequentially with water and saturated brine
  4. filtrationfiltered through a pad of magnesium sulphate
  5. concentrationThe filtrate is concentrated under reduced pressure
  6. customto give the crude product as a pale yellow gum
  7. customThe crude product is purified by column chromatography on silica
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-2dbaa5993faf4c118379b63295cea937
Source dataset
uspto-grants-2012_11
Patent number
US08309739B2

Reaction notes

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