N,N,N',N'-Tetramethylethylenediamine → HCID 123731090, compound

HRID 1746474Notes

Reaction equation

HRID 1746474 reaction equation
[Li]C(CC)C.CN(CCN(C)C)C.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([C:22]([N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[O:23])[CH:19]=[CH:20][CH:21]=1.[Li].[B:30](OC)([O:33]C)[O:31]C>C1COCC1>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[O:23])[C:17]=1[B:30]([OH:33])[OH:31]

Participants

7

Reactant 5

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8470Trimethyl borateHCID 786913Pyrrolidine, 1-(3-methoxybenzoyl)-HCID 3028194LithiumHCID 178418400CID 53628100

Product 1

HCID 123731090HCID 123731090, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

s-BuLi (70 mL, 1.3M in cyclohexane) was added to TMEDA (15.3 g, 131.9 mmol) at −78° C. dropwise within 30 min. After stirring for 20 min, (3-methoxyphenyl)(pyrrolidin-1-yl)methanone (16 g, 78 mmol) in THF (40 mL) was added into the lithium solution slowly. The solution was stirred at −78° C. for 1.5 h and trimethyl borate (36 mL, 322.6 mmol) was added. The mixture was warmed to room temperature and stirred at rt overnight. The solution was acidified to pH=5-6 and the precipitate were filtered. The filter cake was washed with water and ethyl acetate to give 2-methoxy-6-(pyrrolidine-1-carbonyl)phenylboronic acid (5.5 g, 28%) as a white solid.

Workup

  1. stirringThe solution was stirred at −78° C. for 1.5 h
  2. stirringstirred at rt overnight
  3. filtrationthe precipitate were filtered
  4. washThe filter cake was washed with water and ethyl acetate

Sources & evidence

ORD record
ord-d7aa2af60b0b441cb505390fa707cc67
Source dataset
uspto-grants-2015_10
Patent number
US09150526B2

Reaction notes

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