Sodium borohydride → HCID 58790325, compound

HRID 2193680Notes

Reaction equation

HRID 2193680 reaction equation
[F:1][C:2]1[CH:29]=[C:28]([N+:30]([O-])=O)[CH:27]=[CH:26][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:16][CH:15]=3)[S:13][C:6]=12.[BH4-].[Na+]>CO.C1COCC1>[F:1][C:2]1[CH:29]=[C:28]([NH2:30])[CH:27]=[CH:26][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:15]=[CH:16][C:17]([CH2:20][N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:18][CH:19]=3)[S:13][C:6]=12

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 58790077HCID 58790077, compound

Product 1

HCID 58790325HCID 58790325, compoundYield 108.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the nitro compound 53 (256 mg, 0.57 mmol) in a mixture of MeOH (12 mL) and THF (4 mL) at 0° C. was added NiCl2.6H2O (279 mg, 1.14 mmol), followed by portion wise addition of NaBH4 (87 mg, 2.27 mmol). The reaction mixture turned black after 15 min, and was filtered through a celite pad; the filtrate concentrated under reduced pressure. The residue was suspended in 2N HCl and the solids were removed by filteration. The filtrate was basified with NH4OH to pH˜10 then extracted with EtOAc. The organic phase was concentrated to afford the title compound 54 (260 mg, crude, >100% yield, HPLC pure) as yellowish foam. MS (m/z): 420.1 (M+H).

Workup

  1. filtrationwas filtered through a celite pad
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customthe solids were removed by filteration
  4. extractionthen extracted with EtOAc
  5. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-bf7ec401e41e4c768abf64d130efb2d0
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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