Sodium triacetoxyborohydride → HCID 58293454, compound

HRID 1968204Notes

Reaction equation

HRID 1968204 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][C@H:16]([CH:24]([CH3:26])[CH3:25])[C:17]([N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:18].[CH:27]([C:29]1[CH:34]=[CH:33][N:32]=[C:31]2[N:35]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH:36]=[C:37]([C:38]([O:40][CH3:41])=[O:39])[C:30]=12)=O>ClCCCl.C(O)(=O)C>[CH3:25][CH:24]([CH3:26])[C@@H:16]([NH:15][CH2:27][C:29]1[CH:34]=[CH:33][N:32]=[C:31]2[N:35]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH:36]=[C:37]([C:38]([O:40][CH3:41])=[O:39])[C:30]=12)[C:17](=[O:18])[N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 40459151HCID 40459151, compoundHCID 497616131-tert-Butyl 3-methyl 4-formyl-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate

Product 1

HCID 58293454HCID 58293454, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent2×

Procedure

A mixture of sodium triacetoxyborohydride (139 mg, 0.657 mmol) and (R)-2-amino-3-methyl-1-(pyrrolidin-1-yl)butan-1-one (84 mg, 0.493 mmol) in DCE (2 mL) was stirred at room temperature for 30 min. The reaction mixture was cooled to 0° C. A solution of 1-tert-butyl 3-methyl 4-formyl-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate (100 mg, 0.329 mmol) in DCE (2 mL) was added, followed by acetic acid (1 drop). The reaction was stirred at 0° C. for 30 min and then at room temperature for 3 h. Purification by silica column chromatography (EtOAc/DCM, 0-10%) afforded the title compound as a yellow oil (128 mg, 85%). [M+H] calc'd for C24H34N4O5, 459; found, 459.6.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C
  2. stirringThe reaction was stirred at 0° C. for 30 min
  3. waitat room temperature for 3 h
  4. customPurification by silica column chromatography (EtOAc/DCM, 0-10%)

Sources & evidence

ORD record
ord-f50364fd6a934e969b4c6a96f7f94d09
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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