Sodium borohydride → tert-Butyl 9-hydroxy-3-azaspiro[5.5]undecane-3-carboxylate

HRID 1253718Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

NaBH4 (56.18 mmol, 3.0 eq.) was added portionwise to a stirred solution of tert-butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate (18.72 mmol, 1.0 eq.) in MeOH (40 ml) at 0° C. and the resulting reaction mixture was stirred at 25° C. for 1 h. The solvent was evaporated under reduced pressure. The residue was dissolved in MC (100 ml) and washed with water (50 ml) and brine (50 ml). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give the crude product which was used in the next step without further purification. Yield: 95%

Workup

customthe resulting reaction mixture
customThe solvent was evaporated under reduced pressure
dissolutionThe residue was dissolved in MC (100 ml)
washwashed with water (50 ml) and brine (50 ml)
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-10425d476a3b4c6eb0217241111aac26
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455475B2

Reaction notes

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