tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate → HCID 21080214, compound

HRID 346471Notes

Reaction equation

HRID 346471 reaction equation
[CH:1]([Mg]Cl)([CH3:3])[CH3:2].[C:6]([N:13]1[CH2:19][CH2:18][CH2:17][C@H:14]1[CH:15]=[O:16])([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]>>[C:6]([N:13]1[CH2:19][CH2:18][CH2:17][C@H:14]1[C:15](=[O:16])[CH:1]([CH3:3])[CH3:2])([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

3

Reactant 2

HCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylateHCID 178418918HCID 178418918, compound

Product 1

HCID 21080214HCID 21080214, compound

Procedure

30.1 ml (60.2 mmol) 2 M isopropylmagnesium chloride (diethyl ether) and 4.0 g (20.1 mmol) BOC-L-prolinal were allowed to react at −80° C. for 30 min according to procedure F. Yield of the crude product 4.31 g. The product was purified with a silica column using 16% ethyl acetate in petroleum ether as eluent. Yield 1.84 g (7.6 mmol, 38%). The product was oxidized to the corresponding ketone according to procedure G. Yield of crude product 1.59 g. The product was purified with a silica column using 16% ethyl acetate in petroleum ether as eluent. Yield 1.15 g (4.8 mmol, 63%).

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-b6e4aa50115c4124b16d19961d291672
Source dataset
uspto-grants-2007_02
Patent number
US07173024B2

Reaction notes

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