Acetic Acid → tert-Butyl 9-hydroxy-3-azaspiro[5.5]undecane-3-carboxylate

HRID 1808357Notes

Reaction equation

[O:1]=[C:2]1[CH2:19][CH2:18][C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:4][CH2:3]1.[BH4-].[Na+].C(O)(=O)C>C1COCC1>[OH:1][CH:2]1[CH2:3][CH2:4][C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:7][CH2:6]2)[CH2:18][CH2:19]1

Participants

Conditions

Temperature: -5 °C

Procedure

tert-Butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate (1.5 g) was dissolved in THF (7.5 ml) and cooled to −5° C. NaBH4 (0.212 g) was then added and the mixture was stirred for 1 h at room temperature (TLC monitoring). When the conversion was complete, acetic acid was added to the mixture and the methanol was then distilled off. The residue was taken up in water (50 ml) and extracted with ethyl acetate (2×50 ml). The combined organic phases were dried (Na2SO4) and concentrated in vacuo. The resulting crude product was purified by column chromatography (silica gel, 30% ethyl acetate/hexane). Yield: 1.2 g (80%)

Workup

distillationthe methanol was then distilled off
extractionextracted with ethyl acetate (2×50 ml)
dry with materialThe combined organic phases were dried (Na2SO4)
concentrationconcentrated in vacuo
customThe resulting crude product was purified by column chromatography (silica gel, 30% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-2823e149128a42bf990ca5069224bf3b
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357717B2

Reaction notes

Loading…