Boron trifluoride etherate → HCID 58551020, compound

HRID 1907997Notes

Reaction equation

HRID 1907997 reaction equation
[N:1]1([C:6]2[C:7]([OH:12])=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1.CO[C:15]1(OC)[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:17][CH2:16]1.B(F)(F)F.CCOCC.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH:11]1[C:6]2[N:1]3[CH:2]=[CH:3][CH:4]=[C:5]3[C:15]3([CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[O:22])[CH2:17][CH2:16]3)[O:12][C:7]=2[N:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 10340Sodium CarbonateHCID 57714007HCID 57714007, compoundHCID 178517713HCID 178517713, compound

Product 1

HCID 58551020HCID 58551020, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of 3-pyrrol-1-ylpyridin-2-ol (481 mg, 3.00 mmol) and benzyl 4,4-dimethoxypiperidine-1-carboxylate (922 g, 3.3 mol) in CH2Cl2 (20 mL) at 40° C. was added BF3.OEt2 (407.3 μL, 3.300 mmol) drop-wise. The reaction mixture was stirred at 40° C. for 16 hours. The mixture was poured into sat. aq. Na2CO3 and was stirred for 5 min before it was extracted with EtOAc (3×). Organic layers were combined, washed with sat. aq. Na2CO3, water, brine, dried (Na2SO4) and evaporated to dryness. The residue was purified by column chromatography (1-30% EtOAc/CH2Cl2) to give benzyl spiro[piperidine-4,6′-pyrido[2,3-b]pyrrolo[1,2-d][1,4]oxazine]-1-carboxylate as an oil. ESI-MS m/z calc. 375.2. found 376.5 (M+1)+; Retention time: 1.70 minutes (3 min run). 1H NMR (400 MHz, DMSO) δ 8.10 (dd, J=7.7, 1.1 Hz, 1H), 8.00 (dd, J=4.9, 1.5 Hz, 1H), 7.60-7.52 (m, 1H), 7.42-7.36 (m, 4H), 7.36-7.29 (m, 1H), 7.16 (dd, J=7.8, 4.9 Hz, 1H), 6.33 (t, J=3.2 Hz, 1H), 6.20 (d, J=3.4 Hz, 1H), 5.11 (s, 2H), 3.97 (d br, J=13.2 Hz, 2H), 3.28 (s br, 2H), 1.98-1.92 (m, 4H).

Workup

  1. stirringwas stirred for 5 min before it
  2. extractionwas extracted with EtOAc (3×)
  3. washwashed with sat. aq. Na2CO3, water, brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness
  6. customThe residue was purified by column chromatography (1-30% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-d3c7521376c1416bbb2e10bc98774c19
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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