Toluene → HCID 90015494, compound

HRID 626903Notes

Reaction equation

HRID 626903 reaction equation
[CH3:1][C:2]([O-])(C)[CH3:3].[K+].[C:7](=[N:20][CH:21]1[CH2:26][CH2:25][CH2:24][N:23]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:22]1=[O:35])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(Br)C#C.C1(C)C=CC=CC=1>C1COCC1>[C:7](=[N:20][C:21]1([CH2:3][C:2]#[CH:1])[CH2:26][CH2:25][CH2:24][N:23]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:32])([CH3:34])[CH3:33])[C:22]1=[O:35])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 7842Propargyl bromideHCID 23665647Potassium tert-butoxideHCID 90015031HCID 90015031, compound

Product 1

HCID 90015494HCID 90015494, compoundYield 32.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

KOtBu 1.7M in THF (4.32 mL, 7.34 mmol) was added dropwise to a solution of 3-(benzhydrylideneamino)-1-(2-trimethylsilylethoxymethyl)piperidin-2-one (which may be prepared as described in Description 22) (2.5 g, 6.12 mmol) and propargyl bromide 80 wt % in toluene (0.95 mL, 8.57 mmol) in THF (100 mL) at 0° C. under N2. The reaction was stirred for 40 mins. The reaction was quenched by the addition of satd. aq. NaHCO3 and then diluted with EtOAc. The phases were separated, the organic layer was dried (Na2SO4) and the solvent was evaporated to afford an oil. The material was purified by SP4, 100 g SNAP, 0 to 50% EtOAc/i-hexane to afford product: 3-(benzhydrylideneamino)-3-prop-2-ynyl-1-(2-trimethylsilylethoxymethyl)-piperidin-2-one (D23) (897 mg, 2.0082 mmol, 32.8% yield) as a pale yellow oil.

Workup

  1. customThe reaction was quenched by the addition of satd
  2. additionaq. NaHCO3 and then diluted with EtOAc
  3. customThe phases were separated
  4. dry with materialthe organic layer was dried (Na2SO4)
  5. customthe solvent was evaporated
  6. customto afford an oil
  7. customThe material was purified by SP4, 100 g SNAP, 0 to 50% EtOAc/i-hexane
  8. customto afford product

Sources & evidence

ORD record
ord-42e9b1565b2d423e908fae044cc8dfef
Source dataset
uspto-grants-2016_04
Patent number
US09309254B2

Reaction notes

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