Toluene → HCID 67096248, compound

HRID 2076118Notes

Reaction equation

HRID 2076118 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[O:6]1[C:10]2([CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[C:16](Cl)=[O:17])[O:9][CH2:8][CH2:7]1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[O:6]1[C:10]2([CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[C:16]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:17])[O:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 31268PyrrolidineHCID 86054793HCID 86054793, compound

Product 1

HCID 67096248HCID 67096248, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

Pyrrolidine (0.21 mL, 2.5 mmol) was added at 0° C. to a 1 M solution of 1,4-dioxa-spiro[4.5]decane-6-carbonyl chloride in toluene (1 mL, 1 mmol). The mixture was stirred at 20° C. for 1 h, then diluted with ethyl acetate (40 mL), and washed successively with water (10 mL), saturated aquous sodium carbonate solution (10 mL), 1 N hydrochloric acid, and with brine (10 mL). The organic layer was dried over sodium sulfate and evaporated under reduced pressure to give the title compound (97 mg, 41%) as a white solid. MS ISP (m/e): 240.3 (100) [(M+H)+].

Workup

  1. washwashed successively with water (10 mL), saturated aquous sodium carbonate solution (10 mL), 1 N hydrochloric acid
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-eb9e7f15862c4908859571d8e3aa7bc4
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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