Sodium borohydride → HCID 57816766, compound

HRID 2197467Notes

Reaction equation

HRID 2197467 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18].[BH4-].[Na+]>C1COCC1>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:16][CH:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[OH:18]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57816849HCID 57816849, compound

Product 1

HCID 57816766HCID 57816766, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of ethanone prepared in step 1 (60 mg, 0.18 mmol) in THF, was added NaBH4 at room temperature. The reaction was complete after stirring at room temperature for 1 h. The solvent was removed under vacuum and the residue was washed with sat. aq. NaHCO3 solution. The aqueous phase was extracted with DCM. The organic layer was dried over Na2SO4, filtered, concentrated, and purified by silica gel chromatography using a liner gradient of MeOH in DCM as eluent. 1H NMR (CDCl3) δ 3.36 (s, 3H), δ 3.68 (t, 2H), δ 4.07-4.38 (m, 4H), δ 5.12-5.14 (m, 1H), δ 6.36 (bs, 2H), δ 7.26-7.38 (m, 5H), δ 7.51 (s, 1H); MS: 330.1 (M+1).

Workup

  1. customThe solvent was removed under vacuum
  2. washthe residue was washed with sat. aq. NaHCO3 solution
  3. extractionThe aqueous phase was extracted with DCM
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-9802e8e38e5447dfa1f2215341853b36
Source dataset
uspto-grants-2012_12
Patent number
US08338593B2

Reaction notes

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