Dimethylformamide dimethyl acetal → HCID 67065831, compound

HRID 602952Notes

Reaction equation

HRID 602952 reaction equation
[C:1]([N:20]1[CH2:24][CH2:23][C:22](=[O:25])[CH2:21]1)([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:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[CH:28](OC)[N:29]([CH3:31])[CH3:30]>CN(C=O)C>[CH3:28][N:29]([CH:31]=[C:23]1[CH2:24][N:20]([C:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:21][C:22]1=[O:25])[CH3:30]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 67065856HCID 67065856, compound

Product 1

HCID 67065831HCID 67065831, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 1-tritylpyrrolidin-3-one (4.9 g) from Step A in anhydrous DMF (36.0 mL) was dissolved by heating at 80° C. under nitrogen for 10 min. The clear solution was treated with N,N-dimethylformamide dimethyl acetal (18.0 mL) and heated at 80° C. for 12 h. The resulting dark brown solution was evaporated under reduced pressure. The residue was chromatographed on a Biotage® system (silica gel, gradient from 50% to 100% ethyl acetate in hexanes) to yield the title compound. LC-MS=243.1 (M+1).

Workup

  1. dissolutionwas dissolved
  2. temperatureheated at 80° C. for 12 h
  3. customThe resulting dark brown solution was evaporated under reduced pressure
  4. customThe residue was chromatographed on a Biotage® system (silica gel, gradient from 50% to 100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b554bf8661424675a96a42f68d84df4e
Source dataset
uspto-grants-2011_03
Patent number
US07906649B2

Reaction notes

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