Sodium triacetoxyborohydride → HCID 58293435, compound

HRID 1968207Notes

Reaction equation

HRID 1968207 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][C@H:16]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:17]([N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:18].[CH:28]([C:30]1[CH:35]=[CH:34][N:33]=[C:32]2[N:36]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH:37]=[C:38]([C:39]([O:41][CH3:42])=[O:40])[C:31]=12)=O>ClCCCl.C(O)(=O)C>[CH3:26][CH:25]([CH3:27])[CH2:24][C@@H:16]([NH:15][CH2:28][C:30]1[CH:35]=[CH:34][N:33]=[C:32]2[N:36]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH:37]=[C:38]([C:39]([O:41][CH3:42])=[O:40])[C:31]=12)[C:17](=[O:18])[N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 28197509HCID 28197509, compoundHCID 497616131-tert-Butyl 3-methyl 4-formyl-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate

Product 1

HCID 58293435HCID 58293435, compoundYield 102.9%

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-4-methyl-1-(pyrrolidin-1-yl)pentan-1-one (91 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 (100mg, 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 (160 mg, 93%). [M+H] calc'd for C25H36N4O5, 473; found, 473.7.

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-7beef859b6fe46b2a8889a4283c9b9ff
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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