Sodium borohydride → HCID 178501143, compound

HRID 2272655Notes

Reaction equation

HRID 2272655 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH2:9]1)=[O:7].[BH4-].[Na+]>CO.C(OCC)(=O)C.O>[OH:7][CH:6]([C:2]1[S:1][CH:5]=[CH:4][N:3]=1)[C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH2:9]1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 178501142HCID 178501142, compound

Product 1

HCID 178501143HCID 178501143, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl trans-4-(1,3-thiazol-2-ylcarbonyl)cyclohexanecarboxylate (500 mg, 1.97 mmol) in methanol (20 mL) was added sodium borohydride (224 mg, 5.92 mmol) and the solution was stirred for one hour. The solution was then diluted with ethyl acetate and water. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography to afford methyl trans-4-[hydroxy(1,3-thiazol-2-yl)methyl]cyclohexanecarboxylate. MS ESI calc'd. for C12H18NO3S [M+H]+ 256. found 256. 1H NMR (500 MHz, DMSO-d6) δ 7.70 (d, J=3.2 Hz, 1H), 7.58 (d, J=3.2 Hz, 1H), 6.10 (d, J=5.2 Hz, 1H), 4.59 (t, J=5.1 Hz, 1H), 3.54 (s, 3H), 2.21-2.11 (m, 1H), 1.92-1.83 (m, 2H), 1.75-1.64 (m, 1H), 1.64-1.53 (m, 2H), 1.33-1.11 (m, 4H).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-37b06440347e4a82b780fde3bf53e6e6
Source dataset
uspto-grants-2015_09
Patent number
US09120785B2

Reaction notes

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