Sodium borohydride → HCID 178499108, compound

HRID 1518315Notes

Reaction equation

HRID 1518315 reaction equation
[CH:1]([C:3]1[S:7][C:6]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[C:11]([C:18](=[O:37])/[N:19]=[C:20]4/[S:21][C:22]5[CH:36]=[CH:35][CH:34]=[CH:33][C:23]=5[N:24]/4[CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:12]=[CH:13][CH:14]=3)[CH2:9]2)=[N:5][C:4]=1[C:38]([O:40][CH3:41])=[O:39])=[O:2].[BH4-].[Na+]>CO.C1COCC1>[OH:2][CH2:1][C:3]1[S:7][C:6]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[C:11]([C:18](=[O:37])/[N:19]=[C:20]4/[S:21][C:22]5[CH:36]=[CH:35][CH:34]=[CH:33][C:23]=5[N:24]/4[CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:12]=[CH:13][CH:14]=3)[CH2:9]2)=[N:5][C:4]=1[C:38]([O:40][CH3:41])=[O:39]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 178499107HCID 178499107, compound

Product 1

HCID 178499108HCID 178499108, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To compound 45C (2.08 g, 3.42 mmol) in MeOH (50 mL) and THF (20 mL) was added NaBH4 (0.259 g, 6.83 mmol). The reaction mixture was heated at 70° C. for 2 hours. The solvent was removed, and the residue was partitioned between EtOAc and water. The organic layer was isolated, and the aqueous layer was extracted with additional EtOAc. The combined organic layers were washed with brine, dried over MgSO4, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel eluting with 1:1/hexanes:EtOAc to provide 1.86 g of the desired product: 1H NMR (DMSO-d6): δ 8.24-8.26 (m, 1H), 7.94 (d, J=7.67 Hz, 1H), 7.70 (d, J=8.20 Hz, 1H), 7.52-7.56 (m, 1H), 7.34-7.42 (m, 3H), 6.00 (s, 2H), 5.77 (t, J=5.52 Hz, 1H), 5.13 (s, 2H), 4.83 (d, J=5.52 Hz, 2H), 3.67-3.75 (m, 7H), 3.03 (t, J=5.98 Hz, 2H), 0.87-0.91 (m, 2H), −0.18 (s, 9H). MS (ESI(+)): m/z 611 (M+H).

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between EtOAc and water
  3. customThe organic layer was isolated
  4. extractionthe aqueous layer was extracted with additional EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by column chromatography on silica gel eluting with 1:1/hexanes

Sources & evidence

ORD record
ord-daae09617a3047fca59d8342e4feb8b7
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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