Iodine → 2-Methoxy-pyrrolidine-1-carboxylic acid benzyl ester

HRID 132819Notes

Reaction equation

HRID 132819 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1C(O)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19](OC1C(OC(=O)C)=C(I=O)C=CC=1)(=[O:21])C.II.CO>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[O:21][CH3:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 807IodineHCID 887MethanolHCID 101987Benzyloxycarbonyl-L-prolineHCID 21113495Diacetoxyiodosobenzene

Product 1

HCID 109224852-Methoxy-pyrrolidine-1-carboxylic acid benzyl esterYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (S)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (purchased at Fluka, Ref 97090, 6 g, 1.0 eq.) in dichloromethane (300 mL) was added diacetoxyiodosobenzene (15.8 g, 2 eq.) and iodine (3.0 eq., 0.5 eq.). The mixture was stirred 5 h at room temperature. Methanol (12 mL) was added and the reaction mixture was stirred for an additional 1.5 h at room temperature, partitioned between an aqueous solution of sodium sulfite and dichloromethane. The organic layer was washed with an aqueous solution of sodium sulfite, brine, evaporated in vacuo and purified on silica eluting with 9:1 cyclohexane/ethyl acetate to yield 5.0 g (88%) of the desired product as light yellow oil. MS (m/e): 235.5 (MH+, 100%)

Workup

  1. stirringthe reaction mixture was stirred for an additional 1.5 h at room temperature
  2. custompartitioned between an aqueous solution of sodium sulfite and dichloromethane
  3. washThe organic layer was washed with an aqueous solution of sodium sulfite, brine
  4. customevaporated in vacuo
  5. custompurified on silica eluting with 9:1 cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-b86cbbeb5da042a2aaf26fadcae3ef6d
Source dataset
uspto-grants-2008_06
Patent number
US07388095B2

Reaction notes

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