tert-butyl (3S)-3-(hydroxymethyl)pyrrolidine-1-carboxylate → (S)-tert-butyl 3-formylpyrrolidine-1-carboxylate

Reaction equation

CC1(C)N([O])C(C)(C)CCC1.[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][C@H:21]([CH2:24][OH:25])[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]>>[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][C@H:21]([CH:24]=[O:25])[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

Reactant 2

HCID 1514341tert-butyl (3S)-3-(hydroxymethyl)pyrrolidine-1-carboxylate

HCID 2724126Tempo

Product 1

HCID 1514343(S)-tert-butyl 3-formylpyrrolidine-1-carboxylate

Procedure

The alcohol starting materials can be prepared by the 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical (TEMPO) mediated oxidation of (S)-3-hydroxymethylpyrrolidine-1-carboxylic acid t-butyl ester to yield (S)-3-formylpyrrolidine-1-carboxylic acid t-butyl ester.

Sources & evidence

ORD record: ord-1e97e069a2bd40478ba7859d69634d32
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227933B2

Reaction notes

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