Sodium borohydride → 8-Hydroxy-2-[4-((R)-2,2,2-trifluoro-1-methoxy-ethyl)-phenyl]-2-aza-spiro[4.5]decan-1-one

HRID 1023646Notes

Reaction equation

[F:1][C:2]([F:25])([F:24])[C@@H:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:16][CH2:15][C:14]3([CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]3)[C:13]2=[O:23])=[CH:8][CH:7]=1)[O:4][CH3:5].[BH4-].[Na+]>CO>[OH:22][CH:19]1[CH2:18][CH2:17][C:14]2([C:13](=[O:23])[N:12]([C:9]3[CH:8]=[CH:7][C:6]([C@@H:3]([O:4][CH3:5])[C:2]([F:1])([F:24])[F:25])=[CH:11][CH:10]=3)[CH2:16][CH2:15]2)[CH2:21][CH2:20]1

Participants

Conditions

Temperature: 0 °C

Procedure

2-(4-((R)-2,2,2-trifluoro-1-methoxyethyl)phenyl)-2-azaspiro[4.5]decane-1,8-dione (1.15 g) was dissolved in methanol (30 mL) under argon. The mixture was cooled to 0° C. and sodium borohydride (184 mg) was added in three portions to the cold reaction mixture. The mixture was allowed to warm to RT for 2 hours. The reaction mixture was poured into ice/water and was extracted two times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The residue was dried at high vacuum and was used without further purification. Colorless foam (1.2 g), mixture of cis and trans alcohols. MS (ESI): 358.2 (MH+).

Workup

temperatureto warm to RT for 2 hours
extractionwas extracted two times with ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
customthe solvent was evaporated
customThe residue was dried at high vacuum
customwas used without further purification
additionColorless foam (1.2 g), mixture of cis and trans alcohols

Sources & evidence

ORD record: ord-45ded537bd1e41a1ba7caf8b6df9a40b
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722721B2

Reaction notes

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