Sodium borohydride → HCID 59737383, compound

HRID 1907740Notes

Reaction equation

HRID 1907740 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:26])[NH:12][C:13]2[CH:18]=[C:17]([C:19]3[CH2:23][CH2:22][C:21](=[O:24])[CH:20]=3)[CH:16]=[CH:15][C:14]=2[NH2:25])=[CH:7][CH:6]=1)(=O)C.O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+]>C(Cl)Cl.CO>[NH2:25][C:14]1[CH:15]=[CH:16][C:17]([C:19]2[CH2:23][CH2:22][CH:21]([OH:24])[CH:20]=2)=[CH:18][C:13]=1[NH:12][C:11](=[O:26])[C:8]1[CH:7]=[CH:6][C:5]([OH:4])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 21585214Cerium trichloride heptahydrateHCID 59737452HCID 59737452, compound

Product 1

HCID 59737383HCID 59737383, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of amine 260 (0.11 g, 6.31 mmol) in DCM (9 mL) and cerium (III) chloride heptahydrate (0.37 g, 0.93 mmol) in MeOH (6 mL) at −78° C. was added sodium borohydride (60 mg, 0.93 mmol) in one portion. The reaction mixture was allowed to warm to room temperature and stirred for 15 min then concentrated. Purifications by flash chromatography (eluent: 5% MeOH in DCM) followed by chromatotron (same eluent) provided the title compounds 261 (15 mg, 14% yield) and 262 (15 mg, 16% yield).

Workup

  1. concentrationthen concentrated

Sources & evidence

ORD record
ord-7df333d8ce774da796ba8ed358298b48
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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