Sodium borohydride → 2-Hydroxy-3-[2-(2-methoxy-phenyl)-ethyl]-4-oxo-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic Acid Benzyl Ester

HRID 987085Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH:16]2[CH2:17][CH2:18][CH2:19][CH:12]1[C:13](=[O:31])[N:14]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH3:30])[C:15]2=[O:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([O:8][C:9]([N:11]1[CH:12]2[CH2:19][CH2:18][CH2:17][CH:16]1[CH:15]([OH:20])[N:14]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH3:30])[C:13]2=[O:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-[2-(2-Methoxy-phenyl)-ethyl]-2,4-dioxo-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester (Compound 8, 0.77g, 1.82 mmol) was dissolved in methanol (18 mL). The mixture was cooled to 0° C., and NaBH4 (0.14 g, 3.64 mmol) was added in portions from the top. The reaction was stirred for 10 minutes and then carefully quenched with water. MeOH was removed under reduced pressure, and the residue was extracted with EtOAc. The combined organic layers were washed with 10% citric acid (5 mL), water (5 mL), saturated NaHCO3 (5 mL), and brine (5 mL), and finally passed over a short plug of Na2SO4. The solvents were evaporated to give Compound 9 (0.65 g, 83%, mixture of isomers) as a clear oil, which was of sufficiently good quality to be advanced to the next step without further purification. Rf=0.5 (50% EtOAc/hexanes).

Workup

customcarefully quenched with water
customMeOH was removed under reduced pressure
extractionthe residue was extracted with EtOAc
washThe combined organic layers were washed with 10% citric acid (5 mL), water (5 mL), saturated NaHCO3 (5 mL), and brine (5 mL)
customThe solvents were evaporated

Sources & evidence

ORD record: ord-f4c5eb2bbafa452eb794fc12161be196
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06630472B1

Reaction notes

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