Acetonitrile dry ice → HCID 117635647, compound

HRID 1481979Notes

Reaction equation

HRID 1481979 reaction equation
[CH2:1]([O:4][C:5]1([CH3:32])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[CH:17]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:19]=[C:15]3[CH:14]=[C:13]([CH3:25])[C:12]=2[C:26](=[O:31])[C:27]([O:29][CH3:30])=[O:28])[CH2:7][CH2:6]1)[CH:2]=[CH2:3].CB1N2CCC[C@@H]2C(C2C=CC=CC=2)(C2C=CC=CC=2)O1.C1(C)C=CC=CC=1.C(#N)C.C(=O)=O>C1(C)C=CC=CC=1.CCOC(C)=O.C([O-])(O)=O.[Na+]>[CH2:1]([O:4][C:5]1([CH3:32])[CH2:6][CH2:7][N:8]([C:11]2[N:16]3[CH:17]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:19]=[C:15]3[CH:14]=[C:13]([CH3:25])[C:12]=2[C@H:26]([OH:31])[C:27]([O:29][CH3:30])=[O:28])[CH2:9][CH2:10]1)[CH:2]=[CH2:3]

Participants

7

Reactant 3

HCID 86587134Acetonitrile dry iceHCID 86670277(R)-1-methyl-3,3-diphenylhexahydropyrrolo[1,2-c][1,3,2]oxazaborole tolueneHCID 117631542HCID 117631542, compound

Product 1

HCID 117635647HCID 117635647, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
-15 °C

Procedure

To a stirred yellow solution of ethyl 5-(4-(allyloxy)-4-methylpiperidin-1-yl)-6-(2-methoxy-2-oxoacetyl)-7-methylimidazo[1,2-a]pyridine-2-carboxylate (0.86 g, 1.94 mmol, 1 equiv) in toluene (19 mL) was added (R)-1-methyl-3,3-diphenylhexahydropyrrolo[1,2-c][1,3,2]oxazaborole/toluene (0.54 g, 1.94 mmol, 1 equiv). The reaction was cooled to −40° C. (acetonitrile/dry ice bath) and a solution of 50% catechoborane in toluene (0.93 mL, 3.88 mmol, 2 equiv) was added over 10 min. The reaction mixture was stirred at −15° C. for 2 h. Upon completion, the reaction was diluted with EtOAc (30 mL) and sat. NaHCO3 (10 mL). The mixture was stirred vigorously for 30 min. The organic phase was washed with saturated aqueous NaHCO3 (2×5 mL), dried (Na2SO4), and concentrated in vacuo. The crude product was purified by silica gel chromatography (0-10% MeOH/DCM) to afford desired product (0.86 g, 100%) as an off-white solid. LCMS (ESI, M+1): 446.25.

Workup

  1. stirringThe mixture was stirred vigorously for 30 min
  2. washThe organic phase was washed with saturated aqueous NaHCO3 (2×5 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica gel chromatography (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-5064364984cc4f69897a58d8da31bab1
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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