Sodium borohydride → HCID 59754280, compound

HRID 751165Notes

Reaction equation

HRID 751165 reaction equation
[O:1]=[C:2]1[N:6]2[CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C@H:5]2[CH2:4][N:3]1[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([Cl:20])[C:13]=1[CH3:21].[BH4-].[Na+]>CO.CC#N.CCOC(C)=O>[OH:11][C@H:10]1[CH2:9][CH2:8][CH2:7][N:6]2[C:2](=[O:1])[N:3]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([Cl:20])[C:13]=3[CH3:21])[CH2:4][C@H:5]12

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 59754253HCID 59754253, compound

Product 1

HCID 59754280HCID 59754280, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21959252Acetonitrile methanolSolvent

Procedure

A mixture of 78A (5 mg, 0.016 mmol) and sodium borohydride (5 mg) in MeOH:CH3CN (1:1, 1.0 mL) was stirred at rt for 2 h. The reaction was diluted with EtOAc, washed with water (2×2 mL), dried (MgSO4), filtered and concentrated to give the crude product. Purification by chiral preparative HPLC (Chiralpak AD, 25% IPA/heptane isocratic) provided 78B (4 mg): HPLC (Phenomenex Luna 5 u C18 4.6×50 mm, linear gradient over 4 min) retention time 2.40 min (100%); MS (ES) m/z 306 [M+1]+; Chiral analytical HPLC (ChiralPak AD OD 4.6×250 mm, 25% IPA/hexane isocratic) retention time 12.1 min (97.6% ee); MS (ES) m/z 306.1 [M+1]+; HRMS calcd for C15H15ClN3O2 304.0853, Found 304.0846.

Workup

  1. washwashed with water (2×2 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude product
  6. customPurification by chiral preparative HPLC (Chiralpak AD, 25% IPA/heptane isocratic)

Sources & evidence

ORD record
ord-7f40cd2c1c4a4e97875c7f5d47d3d127
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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