Lithium borohydride → HCID 57948949, compound

HRID 1992294Notes

Reaction equation

HRID 1992294 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:27])[CH2:13][CH:12]([C:14](OCC)=[O:15])[S:11][C:10]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[BH4-].[Li+]>O1CCCC1.C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([C@:8]2([CH3:27])[CH2:13][C@@H:12]([CH2:14][OH:15])[S:11][C:10]([NH:19][C:20](=[O:21])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 57948955HCID 57948955, compound

Product 1

HCID 57948949HCID 57948949, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of ethyl 4-(3-bromophenyl)-2-(tert-butoxycarbonylamino)-4-methyl-5,6-dihydro-4H-1,3-thiazine-6-carboxylate (2.0 g, 4.4 mmol) in tetrahydrofuran (87 mL) and ethanol (25 mL) is added lithium borohydride (289 mg, 13.1 mmol, 3 equiv). The reaction is warmed to room temperature and stirred for 4 h. The reaction mixture is quenched with saturated NH4Cl. The layers are separated and the aqueous layer is extracted with ethyl acetate. The combined organic layers are washed with saturated aqueous NaCl and dried over Na2SO4. The mixture is filtered and concentrated to give a light yellow oil. The oil is purified by column chromatography on silica gel (120 g) using a gradient of 0 to 100% ethyl acetate/hexane to give the title compound (29% yield): MS (m/z): 415, 417 (M+1).

Workup

  1. customThe reaction mixture is quenched with saturated NH4Cl
  2. customThe layers are separated
  3. extractionthe aqueous layer is extracted with ethyl acetate
  4. washThe combined organic layers are washed with saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. filtrationThe mixture is filtered
  7. concentrationconcentrated
  8. customto give a light yellow oil
  9. customThe oil is purified by column chromatography on silica gel (120 g)

Sources & evidence

ORD record
ord-5d61fe23bf4b4b3ca46af73b61ecd516
Source dataset
uspto-grants-2010_01
Patent number
US07648983B2

Reaction notes

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