Water → HCID 58489078, compound

HRID 424339Notes

Reaction equation

HRID 424339 reaction equation
[C:1]([NH:4][C@@H:5]([CH2:12]Cl)[C:6]([O:8][CH2:9][CH2:10][CH3:11])=[O:7])(=[O:3])[CH3:2].N1([C:19]2[CH2:23][CH2:22][CH2:21][CH:20]=2)CCCC1.CN(C)CC.[OH2:29]>C(#N)C>[C:1]([NH:4][CH:5]([CH2:12][CH:20]1[CH2:21][CH2:22][CH2:23][C:19]1=[O:29])[C:6]([O:8][CH2:9][CH2:10][CH3:11])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11723DimethylethylamineHCID 81570Pyrrolidine, 1-(1-cyclopenten-1-yl)-HCID 86644964HCID 86644964, compound

Product 1

HCID 58489078HCID 58489078, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

(R)-propyl 2-acetamido-3-chloropropanoate (2.50 g, 12.0 mmol) was dissolved in acetonitrile (25 mL) and 1-pyrrolidino-1-cyclopentene (2.27 mL, 2.14 g, 15.6 mmol) was added. While the reaction was kept at 20° C., dimethylethylamine (1.70 mL, 1.14 g, 15.6 mmol) was added via an addition funnel during 10 min. The homogeneous reaction was stirred at 20° C. for 21 h. Then, water (0.50 mL) was added and the reaction was further stirred for 2.5 h. The solvents were removed in vacuo at 50° C. and the residual oil was purified by silica gel flash chromatography using an EtOAc:petroleum benzene gradient. The product is a yellowish oil. Weight 2.67 g, approx. 87% yield (two diastereomers). 1H NMR: (CDCl3, 300 MHz): δ 6.62 (br d, 0.5H), 6.38 (br d, 0.5H), 4.61-4.49 (m, 1H), 4.05-4.00 (m, 2H), 2.38-1.92 (m, 8H), 1.80-1.47 (m, 6H), 0.90-0.84 (m, 3H).

Workup

  1. customwas kept at 20° C.
  2. customThe homogeneous reaction
  3. stirringthe reaction was further stirred for 2.5 h
  4. customThe solvents were removed in vacuo at 50° C.
  5. customthe residual oil was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-e52baaefa349435a8b2cb631d93a389e
Source dataset
uspto-grants-2012_01
Patent number
US08105807B2

Reaction notes

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