Sodium triacetoxyborohydride → HCID 58293495, compound

HRID 1627131Notes

Reaction equation

HRID 1627131 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][C@H:16]([C:25]([OH:28])([CH3:27])[CH3:26])[C:17]([NH:19][CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:18].[CH:29]([C:31]1[CH:36]=[CH:35][N:34]=[C:33]2[N:37]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH:38]=[C:39]([C:40]([O:42][CH3:43])=[O:41])[C:32]=12)=O>ClCCCl>[CH:20]1([NH:19][C:17](=[O:18])[C@H:16]([NH:15][CH2:29][C:31]2[CH:36]=[CH:35][N:34]=[C:33]3[N:37]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH:38]=[C:39]([C:40]([O:42][CH3:43])=[O:41])[C:32]=23)[C:25]([OH:28])([CH3:26])[CH3:27])[CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 497616131-tert-Butyl 3-methyl 4-formyl-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylateHCID 67225078HCID 67225078, compound

Product 1

HCID 58293495HCID 58293495, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of sodium triacetoxyborohydride (104 mg, 0.493 mmol) and (R)-2-amino-N-cyclopentyl-3-hydroxy-3-methylbutanamide (49.4 mg, 0.246 mmol) in DCE (2 mL) was stirred at room temperature for 30 min. 1-tert-Butyl 3-methyl 4-formyl-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate (75 mg, 0.246 mmol) was added and the reaction mixture was stirred at room temperature for 1 h. Following reaction, the mixture was concentrated to afford the title compound. [M+H] calc'd for C25H36N4O6, 489; found, 489.3.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 1 h
  2. customreaction
  3. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-2bedc12f410f451fa24847f32471a38a
Source dataset
uspto-grants-2014_07
Patent number
US08785429B2

Reaction notes

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