Hydrogen chloride-ethyl acetate → (3aR,6aS)-octahydrocyclopenta[c]pyrrol-5-ylmethanol hydrochloride

Reaction equation

[OH:1][CH2:2][CH:3]1[CH2:17][C@@H:6]2[CH2:7][N:8](C(OC(C)(C)C)=O)[CH2:9][C@@H:5]2[CH2:4]1.[ClH:18].C(OCC)(=O)C>>[ClH:18].[CH2:7]1[C@H:6]2[CH2:17][CH:3]([CH2:2][OH:1])[CH2:4][C@H:5]2[CH2:9][NH:8]1

Participants

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetate

HCID 66669453rel-tert-Butyl (3aR,6aS)-5-(hydroxymethyl)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

Product 1

HCID 86678792(3aR,6aS)-octahydrocyclopenta[c]pyrrol-5-ylmethanol hydrochloride

Procedure

A solution of tert-butyl(3aR,6aS)-5-(hydroxymethyl)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (2.24 g) (WO 2006/14325 A2, 2006) in 4N hydrogen chloride/ethyl acetate (10 mL) was stirred at room temperature for 1 hr. The reaction mixture was concentrated to give the title compound (1.65 g).

Workup

concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record: ord-b8c310b1b81f48c5afb2a122eec8d63e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772277B2

Reaction notes

Loading…