Sodium triacetoxyborohydride → HCID 58293470, compound

HRID 1968196Notes

Reaction equation

HRID 1968196 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][C@@H:16]([CH2:24][CH3:25])[C:17]([N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:18].[CH:26]([C:28]1[CH:33]=[CH:32][N:31]=[C:30]2[N:34]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH:35]=[C:36]([C:37]([O:39][CH3:40])=[O:38])[C:29]=12)=O>ClCCCl.C(O)(=O)C>[O:18]=[C:17]([N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[C@@H:16]([NH:15][CH2:26][C:28]1[CH:33]=[CH:32][N:31]=[C:30]2[N:34]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH:35]=[C:36]([C:37]([O:39][CH3:40])=[O:38])[C:29]=12)[CH2:24][CH3:25]

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 497616131-tert-Butyl 3-methyl 4-formyl-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylateHCID 58293418(2S)-2-Amino-1-(1-pyrrolidinyl)-1-butanone

Product 1

HCID 58293470HCID 58293470, compoundYield 28.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent2×

Procedure

A mixture of sodium triacetoxyborohydride (279 mg, 1.315 mmol) and (S)-2-amino-1-(pyrrolidin-1-yl)butan-1-one (123 mg, 0.789 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 (200 mg, 0.657 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 (83mg, 28.4%). [M+H] calc'd for C23H32N4O5, 445; found, 445.5.

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-14b6d4dbaa0e4296b21a455eea752414
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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