tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate → 111492-61-6

HRID 346468Notes

Reaction equation

HRID 346468 reaction equation
[C:1]1([Mg]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]([N:16]1[CH2:22][CH2:21][CH2:20][C@H:17]1[CH:18]=[O:19])([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]>>[C:9]([N:16]1[CH2:22][CH2:21][CH2:20][C@H:17]1[C:18](=[O:19])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Participants

3

Reactant 2

HCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylateHCID 178478979HCID 178478979, compound

Product 1

HCID 13863568111492-61-6

Procedure

10 ml (20 mmol) 2 M phenylmagnesium chloride (tetrahydrofuran) and 1.99 g (10 mmol) BOC-L-prolinal were allowed to react at −60–40° C. for 60 min according to procedure F. Yield of the crude product 3.06 g. The product was purified with a silica column using 16% ethyl acetate in petroleum ether as eluent. Yield 2.18 g (7.6 mmol, 76%). The product was oxidized to the corresponding ketone according to procedure G. Yield of crude product 3.15 g. The product was purified with a silica column using 20–25% ethyl acetate in petroleum ether as eluent. Yield 1.65 g (6.0 mmol, 79%).

Workup

  1. customto react at −60–40° C. for 60 min
  2. customThe product was purified with a silica column
  3. customThe product was purified with a silica column

Sources & evidence

ORD record
ord-53ba55ecc53f4017b13a4e7e9c856e86
Source dataset
uspto-grants-2007_02
Patent number
US07173024B2

Reaction notes

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