1-Pyrrolidinecarboxylate → benzyl 4-[4-(1-tert-butoxycarbonylpyrrolidin-3(S)-yloxy)phenyl]-3-hydroxypiperidine-1-carboxylate

HRID 1712512Notes

Reaction equation

[OH:1][CH:2]1[CH:7]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:3]1.[N:25]1([C:30]([O-:32])=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26]1>>[C:7]([O:31][C:30]([N:25]1[CH2:29][CH2:28][C@H:27]([O:14][C:11]2[CH:10]=[CH:9][C:8]([CH:7]3[CH2:6][CH2:5][N:4]([C:15]([O:17][CH2:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[O:16])[CH2:3][CH:2]3[OH:1])=[CH:13][CH:12]=2)[CH2:26]1)=[O:32])([CH3:8])([CH3:2])[CH3:6]

Participants

Reactant 2

HCID 223251731-Pyrrolidinecarboxylate

HCID 68500730Benzyl 3-hydroxy-4-(4-hydroxyphenyl)piperidinecarboxylate

Product 1

HCID 68499656benzyl 4-[4-(1-tert-butoxycarbonylpyrrolidin-3(S)-yloxy)phenyl]-3-hydroxypiperidine-1-carboxylate

Procedure

Analogously to Method I, 0.665 g of benzyl 3-hydroxy-4-(4-hydroxyphenyl)piperidine-1-carboxylate and 0.822 g of tert-butyl 3(R)-toluene-4-sulphonyloxy)pyrrolidine-1-carboxylate are reacted. The title compound is obtained as a white foam. Rf=0.14 (1:1 EtOAc-heptane). Rt=4.91.

Sources & evidence

ORD record: ord-f5b892de3fdb44d38c57b16015f0beba
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790715B2

Reaction notes

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