(S)-(-)-N-Boc-prolinol → 1,1-Dimethylethyl (2S,4S)-4-(((1,1-dimethylethyl)dimethylsilyl)oxy)-2-formyl-1-pyrrolidinecarboxylate

HRID 923708Notes

Reaction equation

HRID 923708 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][C@@H:13]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH2:12][C@H:9]1[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N1CCC[C@H]1CO)=O)(C)(C)C>>[C:1]([O:5][C:6]([N:8]1[CH2:14][C@@H:13]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:17])[CH3:18])[CH2:12][C@H:9]1[CH:10]=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 643448(S)-(-)-N-Boc-prolinolHCID 58303448tert-butyl (2S,4S)-4-[tert-butyl(dimethyl)silyl]oxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 577540071,1-Dimethylethyl (2S,4S)-4-(((1,1-dimethylethyl)dimethylsilyl)oxy)-2-formyl-1-pyrrolidinecarboxylate

Procedure

With the exception that N-t-butoxycarbonyl-cis-4-(t-butyldimethylsilyl)oxy-L-prolinol, instead of N-t-butoxycarbonyl-L-prolinol, was used, the same procedure as in Preparation Example 1-1 was repeated to afford the title compound. 3.8 g (52%).

Workup

  1. customthe same procedure as in Preparation Example 1-1

Sources & evidence

ORD record
ord-026e420b7dd74a0396f2a7ffa73d718e
Source dataset
uspto-grants-2016_03
Patent number
US09278996B2

Reaction notes

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