Methanol → HCID 86723489, compound

HRID 2201252Notes

Reaction equation

HRID 2201252 reaction equation
[BH4-].[Na+].[CH3:3][N:4]1[C:9]2=[C:10]3[N:15]([C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[C:8]2[C:7](=[O:27])[N:6]([CH3:28])[C:5]1=[O:29])[C@H:14]([C:23]([OH:25])=[O:24])[CH2:13][CH2:12][C:11]3=[O:26].[CH3:30]O>>[OH:26][CH:11]1[C:10]2[N:15]([C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:8]3[C:7](=[O:27])[N:6]([CH3:28])[C:5](=[O:29])[N:4]([CH3:3])[C:9]3=2)[C@H:14]([C:23]([O:25][CH3:30])=[O:24])[CH2:13][CH2:12]1

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86723487HCID 86723487, compound

Product 1

HCID 86723489HCID 86723489, compound

Procedure

Sodium borohydride (0.179 g, 4.72 mmol) was added slowly to a suspension of (S)-1,3-dimethyl-2,4,10-trioxo-5-phenyl-1,2,3,4,7,8,9,10-octahydropyrimido[4,5-a]indolizine-7-carboxylic acid (1.8 g, 4.72 mmol) in methanol (40 mL). The mixture was stirred at room temperature for 30 mins. The reaction was quenched with saturated NaHCO3(aq) and extracted with DCM. The organic phase was passed through a hydrophobic frit and evaporated under vacuum to afford the title compound.

Workup

  1. customThe reaction was quenched with saturated NaHCO3(aq)
  2. extractionextracted with DCM
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-ed54f8819e1643fb81f106f385ca9800
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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