(R)-tert-Butyl 3-(tosyloxy)pyrrolidine-1-carboxylate → benzyl 4-[4-(1-tert-butoxycarbonylpyrrolidin-3(S)-yloxy)phenyl]-3-hydroxypiperidine-1-carboxylate

HRID 1176516Notes

Reaction equation

HRID 1176516 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.C1(C)C=CC(S(O[C@@H:35]2[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36]2)(=O)=O)=CC=1>>[C:43]([O:42][C:40]([N:37]1[CH2:38][CH2:39][C@H:35]([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)[CH2:36]1)=[O:41])([CH3:46])([CH3:44])[CH3:45]

Participants

3

Reactant 2

HCID 23560883(R)-tert-Butyl 3-(tosyloxy)pyrrolidine-1-carboxylateHCID 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-bf2f0a0e111c452ab122fb48f1f3683f
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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