N-Boc-pyrrolidine → (S)-1-N-Boc-piperidine-2-ethanol

Reaction equation

[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N1CCCC1)([O:16][C:17](C)(C)[CH3:18])=O.CN1C[C@@H]2[C@H]3N(C[C@@H](C2)C1)CCCC3>>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]1[CH2:18][CH2:17][OH:16])=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

Reactant 3

HCID 643455N-Boc-pyrrolidine

HCID 7010304N-(tert-butoxycarbonyl)piperidine

HCID 11310084(1R,2S,9S)-(+)-11-Methyl-7,11-diazatricyclo[7.3.1.02,7]tridecane

Product 1

HCID 1514243(S)-1-N-Boc-piperidine-2-ethanol

Procedure

This compound is prepared in a manner analogous to that described in Example 3, but 1-Boc-piperidine is used insead of 1-Boc-pyrrolidine, and (+)-sparteine surrogate is used instead of (−)-sparteine.