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

HRID 1864509Notes

Reaction equation

HRID 1864509 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, 1H), 2.0 (m, 1H), 2.5 (m, 2H), 3.2 (m, 2H), 3.3 (m, 1H), 3.5 (m, 1H), 3.6 (m, 1H), 4.1 (m, 1H), 8.7 (s, 1H), 9.5 (m, 1H). ES+=117.97.

Sources & evidence

ORD record
ord-6b703e435b54497e97a421a205593baa
Source dataset
uspto-grants-2009_12
Patent number
US07625909B2

Reaction notes

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