Isobutyraldehyde → HCID 57953790, compound

HRID 1094540Notes

Reaction equation

HRID 1094540 reaction equation
N1CCCCC1.[CH:7]1([C:13]2[C:14]3[CH:15]=[CH:16][C:17]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[CH:18][C:19]=3[N:20]3[CH2:26][C:25]([C:27](=[O:34])[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:24][C:23]4[CH:35]=[C:36]([O:39][CH3:40])[CH:37]=[CH:38][C:22]=4[C:21]=23)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[CH:48](=O)[CH:49]([CH3:51])[CH3:50]>CCO>[CH:7]1([C:13]2[C:14]3[CH:15]=[CH:16][C:17]([C:41]([O:43][C:44]([CH3:46])([CH3:45])[CH3:47])=[O:42])=[CH:18][C:19]=3[N:20]3[CH2:26][C:25]([C:27](=[O:34])/[C:28](/[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:48]/[CH:49]([CH3:51])[CH3:50])=[CH:24][C:23]4[CH:35]=[C:36]([O:39][CH3:40])[CH:37]=[CH:38][C:22]=4[C:21]=23)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 6561IsobutyraldehydeHCID 8082Piperidine2×HCID 59133793HCID 59133793, compound

Product 1

HCID 57953790HCID 57953790, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Piperidine (17 μL, 0.18 mmol) was added to a stirring solution of tert-butyl 13-cyclohexyl-6-(3-ethoxy-3-oxopropanoyl)-3-methoxy-7H-indolo[2,1-a][2]benzazepine-10-carboxylate (1.0 g, 1.79 mmol) and isobutyraldehyde (16.4 mL, 179 mmol) in EtOH (9 mL) at room temperature. After 3 hrs of stirring an additional amount of piperidine (38 μL, 0.40 mmol) was added and the reaction was allowed to stir overnight at room temperature. The mixture was concentrated and was purified on silica gel (BIOTAGE®, EtOAc/hexanes gradient, fraction collection at λ=254 nm) to give the titled compound (950 mg, 1.55 mmol, 87% yield) consistent by LCMS and NMR as a yellow foamy sticky solid.

Workup

  1. additionwas added
  2. concentrationThe mixture was concentrated
  3. customwas purified on silica gel (BIOTAGE®, EtOAc/hexanes gradient, fraction collection at λ=254 nm)

Sources & evidence

ORD record
ord-cf0876e6ba8949608cd4b3f0f77d78ff
Source dataset
uspto-grants-2012_03
Patent number
US08133884B2

Reaction notes

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