Methyl chloroformate → HCID 67015385, compound

HRID 1377765Notes

Reaction equation

HRID 1377765 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH2:19][CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:11]=2)[CH2:8][NH:7][CH2:6]1)=[O:4].Cl[C:30]([O:32][CH3:33])=[O:31]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOCC>[CH3:33][O:32][C:30]([N:7]1[CH2:8][C@@H:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH2:19][CH2:20][CH2:21][O:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:11]=2)[C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6]1)=[O:31]

Participants

6

Reactant 2

HCID 6586Methyl chloroformateHCID 22915246HCID 22915246, compound

Product 1

HCID 67015385HCID 67015385, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methoxycarbonyl-4-[3-(3-phenoxypropoxy)-4-methoxyphenyl]pyrrolidine (720 mg, 1.87 mmol) in 5 mL of CH2Cl2 at 0° C. was added DMAP (275 mg, 2.25 mmol), followed by methyl chloroformate (213 mg, 2.25 mmol). The solution was stirred for 2 hr, diluted with ether, and washed with 1M H3PO4. The aqueous layer was extracted with ether (2×) and ethyl acetate (1×). The combined organic layers were dried over MgSO4, filtered and concentrated to a colorless oil. Silica gel chromatography (4:2:1, hexanes:ethyl acetate:CH2Cl2) provided trans-1-methoxycarbonyl-3-methoxycarbonyl-4-[3-(3-phenoxypropoxy)-4-methoxyphenyl]pyrrolidine as a colorless oil (634 mg, 77%). Anal. Calcd for C24H29NO7 : C, 64.99; H, 6.59; N, 3.16. Found: C, 64.85; H, 6.57; N, 3.15.

Workup

  1. washwashed with 1M H3PO4
  2. extractionThe aqueous layer was extracted with ether (2×) and ethyl acetate (1×)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a colorless oil

Sources & evidence

ORD record
ord-2c2f136355d944138f650164bb2eb807
Source dataset
uspto-grants-1997_09
Patent number
US05665754

Reaction notes

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