tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate → Tert-butyl (2S)-2-acetylpyrrolidine-1-carboxylate

HRID 346469Notes

Reaction equation

HRID 346469 reaction equation
[CH3:1][Mg]Cl.[C:4]([N:11]1[CH2:17][CH2:16][CH2:15][C@H:12]1[CH:13]=[O:14])([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]>>[C:4]([N:11]1[CH2:17][CH2:16][CH2:15][C@H:12]1[C:13](=[O:14])[CH3:1])([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]

Participants

3

Reactant 2

HCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylateHCID 178418332HCID 178418332, compound

Product 1

HCID 10465808Tert-butyl (2S)-2-acetylpyrrolidine-1-carboxylate

Procedure

25 ml (75 mmol) 3 M methylmagnesium chloride (diethyl ether) and 8.25 g (41.4 mmol) BOC-L-prolinal were allowed to react at −80° C. for 30 min according to procedure F. Yield of the crude product 9.19 g. The product was purified with a silica column using 33% ethyl acetate in petroleum ether as eluent. Yield 7.54 g (35.0 mmol 85%). The product was oxidized to the corresponding ketone according to procedure G. Yield of crude product 6.91 g. The product was purified with a silica column using 20–25% ethyl acetate in petroleum ether as eluent. Yield 5.61 g (26.3 mmol, 75%).

Workup

  1. customto react at −80° C. for 30 min
  2. customThe product was purified with a silica column
  3. customThe product was purified with a silica column

Sources & evidence

ORD record
ord-201f7ab94c124c3b8eee44a569b0fb0c
Source dataset
uspto-grants-2007_02
Patent number
US07173024B2

Reaction notes

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