N-(tert-Butoxycarbonyl)-D-prolinol → N-(tert-Butoxycarbonyl)-D-prolinal

Reaction equation

[C:1]([N:8]1[CH2:14][CH2:13][CH2:12][C@@H:9]1[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N1CCC[C@H]1CO)(OCC1C=CC=CC=1)=O>>[C:1]([N:8]1[CH2:14][CH2:13][CH2:12][C@@H:9]1[CH:10]=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

Reactant 2

HCID 688279N-(tert-Butoxycarbonyl)-D-prolinol

HCID 11096562Cbz-L-Prolinol

Product 1

HCID 7009153N-(tert-Butoxycarbonyl)-D-prolinal

Procedure

(R)-N-Boc-2-Formyl-pyrrolidine was prepared by Swern oxidation of (R)-N-Boc prolinol (Fluka) using the procedure for the oxidation of CBZ-prolinol described by of M. G. B. Drew et al. supra.

Sources & evidence

ORD record: ord-2f7c734ca9914415bb315bd9efdb0188
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06130239

Reaction notes

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