Sodium triacetoxyborohydride → HCID 58293479, compound

HRID 1968220Notes

Reaction equation

HRID 1968220 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][C@H:16]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:17]([OH:19])=[O:18].[CH:24]([C:26]1[CH:31]=[CH:30][N:29]=[C:28]2[N:32]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH:33]=[C:34]([C:35]([O:37][CH3:38])=[O:36])[C:27]=12)=O>C(Cl)Cl>[C:42]([O:41][C:39]([N:32]1[C:28]2=[N:29][CH:30]=[CH:31][C:26]([CH2:24][NH:15][C@H:16]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:17]([OH:19])=[O:18])=[C:27]2[C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33]1)=[O:40])([CH3:45])([CH3:44])[CH3:43]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 6950340D-tert-leucineHCID 497616131-tert-Butyl 3-methyl 4-formyl-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate

Product 1

HCID 58293479HCID 58293479, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 10 mL round bottom flask was added sodium triacetoxyborohydride (104 mg, 0.493 mmol), (R)-2-amino-3,3-dimethylbutanoic acid (43.1 mg, 0.329 mmol) and DCM (2 mL). The reaction mixture were stirred at room temperature in for 30 min after which was added 1-tert-butyl 3-methyl 4-formyl-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate (50 mg, 0.164 mmol) in DCM (2 mL). The reaction was stirred at room temperature for 2 h and then quenched with MeOH (3 drops). The mixture was concentrated to afford the title compound, which was used in the next step without further purification. [M+H] calc'd for C21H29N3O6, 420; found, 420.3.

Workup

  1. stirringThe reaction was stirred at room temperature for 2 h
  2. customquenched with MeOH (3 drops)
  3. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-61b2ffd14efd41c086a020961b8fedec
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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