Sodium triacetoxyborohydride → HCID 58293432, compound

HRID 1627117Notes

Reaction equation

HRID 1627117 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][C@H:16]([C@H:25]([CH3:28])[CH2:26][CH3:27])[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@H:25]([CH3:28])[CH2:26][CH3:27])[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 28202225HCID 28202225, compoundHCID 497616131-tert-Butyl 3-methyl 4-formyl-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate

Product 1

HCID 58293432HCID 58293432, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of sodium triacetoxyborohydride (104 mg, 0.493 mmol) and (2R,3R)-2-amino-N-cyclopentyl-3-methylpentanamide (48.9 mg, 0.246 mmol) in DCE (2 mL) was stirred at room temperature for 30 min. To this mixture was added 1-tert-butyl 3-methyl 4-formyl-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate (75 mg, 0.246 mmol). The reaction mixture was stirred at room temperature for 1 h and was subsequently concentrated to afford the title compound as a crude intermediate. [M+H] calc'd for C26H38N4O5, 487; found, 487.7.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 h
  2. concentrationwas subsequently concentrated

Sources & evidence

ORD record
ord-33d9d38753ab4d189be976df3b1e2283
Source dataset
uspto-grants-2014_07
Patent number
US08785429B2

Reaction notes

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