Ethyl diazoacetate → HCID 59450534, compound

HRID 1948661Notes

Reaction equation

HRID 1948661 reaction equation
C1([C@@H]2COC=N2)C=CC=CC=1.[C:12]([O:20][C:21]1[CH:29]=[C:28]2[C:24]([CH:25]=[CH:26][CH2:27]2)=[CH:23][CH:22]=1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[N+](=[CH:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[N-]>ClCCl>[C:12]([O:20][C:21]1[CH:22]=[CH:23][C:24]2[C@@H:25]3[C@@H:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[C@@H:26]3[CH2:27][C:28]=2[CH:29]=1)(=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 12192Ethyl diazoacetateHCID 12254976HCID 12254976, compoundHCID 59450529HCID 59450529, compound

Product 1

HCID 59450534HCID 59450534, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(+)-2,2′-Isopropylidenebis[(4R)-4-phenyl-2-oxazoline (849 mg, 2.542 mmol) was added to a stirring solution of 1H-inden-6-yl benzoate from Step D (30 g, 127.119 mmol) and Cu(I) triflate (657 mg, 1.271 mmol) in dichloromethane (300 mL) at rt under nitrogen. The solution was stirred at rt for 4 h. A solution of ethyl diazoacetate (29 g, 254.237 mmol) in dichloromethane (100 mL) was added at it through a syringe pump over a period of 72 h. Solvent was removed under reduce pressure, and the residue was purified by column chromatography on silica gel (PE) to give the title compound (about 50% enantiomeric excess). 1H-NMR (400 MHz, CDCl3): δ 8.18 (d, J=7.1 Hz, 2H), 7.63 (t, J=7.6 Hz, 1H), 7.51 (t, J=7.1 Hz, 2H), 7.37 (d, J=8.1 Hz, 1H), 6.96-7.02 (m, 2H), 4.16 (q, J=7.1 Hz, 2H), 3.29-3.35 (m, 1H), 2.95-3.10 (m, 2H), 2.46-2.50 (m, 1H), 1.26-1.33 (m, 4H) ppm. MS: m/z 323.2 (M+1)+.

Workup

  1. customSolvent was removed
  2. customthe residue was purified by column chromatography on silica gel (PE)

Sources & evidence

ORD record
ord-27c645e329794633abe82ca566dbef22
Source dataset
uspto-grants-2013_03
Patent number
US08399507B2

Reaction notes

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