Sodium borohydride → Tert-butyl 9-(2-hydroxyethoxy)-3-azaspiro[5.5]undecane-3-carboxylate

HRID 1253721Notes

Reaction equation

[BH4-].[Na+].[O:3]=[CH:4][CH2:5][O:6][CH:7]1[CH2:24][CH2:23][C:10]2([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH2:9][CH2:8]1>CO>[OH:3][CH2:4][CH2:5][O:6][CH:7]1[CH2:24][CH2:23][C:10]2([CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:14][CH2:15]2)[CH2:9][CH2:8]1

Participants

Conditions

Temperature: 25 °C

Procedure

NaBH4 (13.46 mmol, 2.0 eq.) was added portion wise to a stirred solution of tert-butyl 9-(2-oxoethoxy)-3-azaspiro[5.5]undecane-3-carboxylate (6.73 mmol, 1.0 eq.) in MeOH (65 ml) at 0° C. and the resulting reaction mixture was stirred at 25° C. for 16 h. The solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate (300 ml) and washed with water (200 ml) and brine (200 ml). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography eluting with 20% ethyl acetate in hexanes to give the desired product as a yellow sticky solid. Yield: 40%

Workup

customthe resulting reaction mixture
customThe solvent was evaporated under reduced pressure
dissolutionThe residue was dissolved in ethyl acetate (300 ml)
washwashed with water (200 ml) and brine (200 ml)
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure
customto give the crude product
customThe crude product was purified by silica gel column chromatography
washeluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-c0815286f4cd4c0baf17e42dd44103ce
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455475B2

Reaction notes

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