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Formaldehyde → (1-(1-Methylpiperidin-4-yl)-1H-pyrazol-4-yl)boronic acid pinacol ester

HRID 389455
Notes
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Reaction equation

HRID 389455 reaction equation
[CH3:1][C:2]1([CH3:20])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][N:12]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH:13]=2)[O:3]1.[CH2:21]=O.[BH4-].[Na+]>CO>[CH3:21][N:17]1[CH2:18][CH2:19][CH:14]([N:12]2[CH:13]=[C:9]([B:4]3[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:20])([CH3:1])[O:3]3)[CH:10]=[N:11]2)[CH2:15][CH2:16]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 57812229HCID 57812229, compound

Product 1

HCID 59231689(1-(1-Methylpiperidin-4-yl)-1H-pyrazol-4-yl)boronic acid pinacol ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine (0.500 g, 1.80 mmol) and 37% aqueous formaldehyde solution (0.269 mL, 3.61 mmol) in MeOH (10.0 mL) were combined and stirred at 40° C. for 2 h. Then sodium borohydride (205 mg, 5.41 mmol) was carefully added to the reaction mixture left to stir for 16 h. The reaction was concentrated in vacuo to a solid. The crude product was dissolved in EtOAc and washed with water several times. The organic layer was collected, dried with sodium sulfate, filtered and concentrated in vacuo to a solid to yield the desired product. 1H NMR (400 MHz, CD3OD): δ 7.90 (s, 1H), 7.67 (s, 1H), 4.16-4.26 (m, 1H), 3.00 (d, J=12.13 Hz, 2H), 2.34 (s, 3H), 2.25 (td, J=11.75, 3.28 Hz, 2H), 2.03-2.15 (m, 4H), 1.31 (s, 12H).

Workup

  1. waitleft
  2. stirringto stir for 16 h
  3. concentrationThe reaction was concentrated in vacuo to a solid
  4. dissolutionThe crude product was dissolved in EtOAc
  5. washwashed with water several times
  6. customThe organic layer was collected
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo to a solid

Sources & evidence

ORD record
ord-ef66cb78623b4daa81e4bcb15db84b3a
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08378104B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes