(2S,3S)-1-(tert-Butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid → HCID 67323751, compound

HRID 1401785Notes

Reaction equation

HRID 1401785 reaction equation
Cl.[CH3:2][C:3]1([CH3:26])[CH2:12][CH2:11][C:10]([CH3:14])([CH3:13])[C:9]2[CH:8]=[C:7]([C:15]3[N:16]=[C:17]([CH:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[S:18][CH:19]=3)[CH:6]=[CH:5][C:4]1=2.C(OC([N:34]1[CH2:38][CH2:37][C@H:36]([OH:39])[C@H:35]1[C:40](O)=[O:41])=O)(C)(C)C>CS(C)=O>[OH:39][C@H:36]1[CH2:37][CH2:38][NH:34][C@@H:35]1[C:40]([N:23]1[CH2:24][CH2:25][CH:20]([C:17]2[S:18][CH:19]=[C:15]([C:7]3[CH:6]=[CH:5][C:4]4[C:3]([CH3:26])([CH3:2])[CH2:12][CH2:11][C:10]([CH3:13])([CH3:14])[C:9]=4[CH:8]=3)[N:16]=2)[CH2:21][CH2:22]1)=[O:41]

Participants

4

Reactant 2

HCID 14037017(2S,3S)-1-(tert-Butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acidHCID 67166643HCID 67166643, compound

Product 1

HCID 67323751HCID 67323751, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The preparation was carried out analogously starting from 150 mg (0.36 mmol) of 4-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidine hydrochloride and 94 mg (0.40 mmol) of (2S,3S)-3-hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester in DMSO. The product was purified by means of flash chromatography on silica gel. The protecting group was cleaved off analogously using HCl in methanol. The product is in the form of the hydrochloride.

Workup

  1. customThe product was purified by means of flash chromatography on silica gel

Sources & evidence

ORD record
ord-17d97157eaec4746b1d6c44714c269f4
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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