Acetic Acid → HCID 17756290, compound

To (S)-2-(2-chloro-5-nitro-phenoxymethyl)-pyrrolidine (4.82 g, 18.77 mmol) in 167 mL CH3CN at RT was added 37% aqueous formaldehyde (7.58 mL) then NaCNBH3 (1.887 g, 30.03 mmol). The reaction was stirred for 1 h, as the reaction pH was adjusted every 10 min to about 7 by adding small amounts of HOAc. The reaction was concentrated to small aqueous volume and dissolved in 2 N NaOH (aq) and Et2O. The layers were separated, and the organic layer was washed twice with 2 N NaOH then extracted twice with 1 N HCl (aq). The combined acidic aqueous layers were basified to pH>12 with solid NaOH and extracted 3 times with EtOAc. The EtOAc layers were washed once with 2 N NaOH and then once with mix of brine and 2 N NaOH, combined, dried over Na2SO4, filtered, and concentrated to dryness, to yield the title compound.

1. waitwas adjusted every 10 min to about 7
2. concentrationThe reaction was concentrated to small aqueous volume
3. dissolutiondissolved in 2 N NaOH (aq)
4. customThe layers were separated
5. washthe organic layer was washed twice with 2 N NaOH
6. extractionthen extracted twice with 1 N HCl (aq)
7. extractionextracted 3 times with EtOAc
8. washThe EtOAc layers were washed once with 2 N NaOH
9. additiononce with mix of brine and 2 N NaOH
10. dry with materialdried over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated to dryness

ORD record

ord-f615bbb393bf4522ac0234886dc1706f

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07531553B2