tert-butyl (2R,3S)-3-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate → 2-Pyrrolidinemethanol, 3-hydroxy-, hydrochloride, (2R,3S)-

HRID 2221015Notes

Reaction equation

HRID 2221015 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][N:4](C(OC(C)(C)C)=O)[C@@H:3]1[CH2:14][OH:15].[ClH:16].C[C@H]1CCN[C@@H]1CO>>[ClH:16].[OH:15][CH2:14][C@@H:3]1[C@@H:2]([OH:1])[CH2:6][CH2:5][NH:4]1

Participants

3

Reactant 2

HCID 10910976tert-butyl (2R,3S)-3-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylateHCID 57463460HCID 57463460, compound

Product 1

HCID 156073442-Pyrrolidinemethanol, 3-hydroxy-, hydrochloride, (2R,3S)-

Procedure

The title compound was prepared from 1,1-dimethylethyl (2R,3S)-3-hydroxy-2-(hydroxymethyl)-1-pyrrolidinecarboxylate using the methods used to prepare [(2S,3S)-3-methyl-2-pyrrolidinyl]methanol hydrochloride. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.8 (m, 1 H) 2.0 (m, 1H) 2.5 (m, 2 H) 3.2 (m, 2 H) 3.3 (m, 1 H) 3.5 (m, 1 H) 3.6 (m, 1 H) 4.1 (m, 1 H) 8.7 (s, 1 H) 9.5 (m, 1 H). ES+=117.97.

Sources & evidence

ORD record
ord-4bc134e10003448c83736c95cc458cc9
Source dataset
uspto-grants-2008_05
Patent number
US07368453B2

Reaction notes

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