Sodium triacetoxyborohydride → HCID 58293467, compound

HRID 1968222Notes

Reaction equation

HRID 1968222 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][C@H:16]([CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)[C:17]([OH:19])=[O:18].[CH:25]([C:27]1[CH:32]=[CH:31][N:30]=[C:29]2[N:33]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH:34]=[C:35]([C:36]([O:38][CH3:39])=[O:37])[C:28]=12)=O>C(Cl)Cl>[C:43]([O:42][C:40]([N:33]1[C:29]2=[N:30][CH:31]=[CH:32][C:27]([CH2:25][NH:15][C@H:16]([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[C:17]([OH:19])=[O:18])=[C:28]2[C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34]1)=[O:41])([CH3:46])([CH3:45])[CH3:44]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 10351805(αR)-α-Aminocyclopentaneacetic acidHCID 497616131-tert-Butyl 3-methyl 4-formyl-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate

Product 1

HCID 58293467HCID 58293467, 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-2-cyclopentylacetic acid (47.1 mg, 0.329 mmol) and DCM (2 mL). The reaction mixture was stirred at room temperature 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 C22H29N3O6, 432; found, 432.4.

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-b35815f80c41459f8efab95786a6a2ca
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

Loading…