1-Benzyl 2-methyl 4-methoxypyrrolidine-1,2-dicarboxylate → Benzyl 2-(1-hydroxycyclopropyl)-4-methoxypyrrolidine-1-carboxylate

HRID 1852742Notes

Reaction equation

HRID 1852742 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[CH3:5][O:6][CH:7]1[CH2:11][N:10]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH:9]([C:22]([O:24]C)=O)[CH2:8]1>C(OCC)C.[Cl-].[NH4+].CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[OH:24][C:22]1([CH:9]2[CH2:8][CH:7]([O:6][CH3:5])[CH2:11][N:10]2[C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])[CH2:2][CH2:1]1

Participants

6

Reactant 2

HCID 140361701-Benzyl 2-methyl 4-methoxypyrrolidine-1,2-dicarboxylateHCID 178418443HCID 178418443, compound

Product 1

HCID 86724493Benzyl 2-(1-hydroxycyclopropyl)-4-methoxypyrrolidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 25517Ammonium ChlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

A 3M solution of ethylmagnesium bromide (1.43 mL, 4.30 mmol) was added over a period of 40-60 minutes under stirring to a room temperature solution of 1-benzyl 2-methyl 4-methoxypyrrolidine-1,2-dicarboxylate (420 mg, 1.43 mmol) and titanium (IV) isopropoxide (0.086 mL, 0.286 mmol) in diethyl ether. The mixture was stirred for 1 hour at room temperature. The reaction was cooled to 0° C., treated with a few drops of saturated aqueous ammonium chloride, filtered through celite, and washed with diethyl ether. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford benzyl 2-(1-hydroxycyclopropyl)-4-methoxypyrrolidine-1-carboxylate. MS ESI calc'd. for C16H21Na4 [M+H]+ 292. found 292.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. filtrationfiltered through celite
  3. washwashed with diethyl ether
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5ac0145188e74ec1b6c7c70aefcbfd9f
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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