Sodium triacetoxyborohydride → HCID 58293538, compound

HRID 1968273Notes

Reaction equation

HRID 1968273 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.[NH2:16][C@H:17]([CH2:25][CH3:26])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].[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:21]([O:20][C:18](=[O:19])[C@H:17]([NH:16][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)[CH2:25][CH3:26])([CH3:22])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 497616131-tert-Butyl 3-methyl 4-formyl-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylateHCID 74889732959750-74-4

Product 1

HCID 58293538HCID 58293538, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

Sodium triacetoxyborohydride (9.86 mmol) and (R)-tert-butyl 2-aminobutanoate hydrochloride (5.59 mmol) were added to a 100 mL round bottom flask, followed by DCE (20 mL). The reaction mixture was stirred at room temperature for 30 min and cooled to 0° C. A solution of 1-tert-butyl 3-methyl 4-formyl-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate (3.29 mmol) in DCE (20 mL) was added. The reaction mixture was stirred at 0° C. for 30 min and at room temperature for 3 h. Purification by silica column chromatography (EtOAc/DCM, 0-10%) afforded the title compound as a yellow oil (1.4 g, 95%). [M+H] calc'd for C23H33N3O6, 448; found, 448.6.

Workup

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

Sources & evidence

ORD record
ord-f80bf46272d04576bf4f2c6971e32b67
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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