Sodium Bicarbonate → HCID 68819514, compound

HRID 736769Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3-(1-phenyl-ethylamino)-7-aza-bicyclo[2.2.1]hept-2-ene-2,7-dicarboxylic acid 7-tert-butyl ester 2-methyl ester (0.3 g, 0.81 mmol) in acetic acid-acetonitrile (1:1, 20 mL) was treated with sodium triacetoxyborohydride (0.19 g, 0.89 mmol), stirred for 5 h at 0° C. and then neutralized with saturated aqueous sodium bicarbonate (5 mL). The organic layer was washed with brine (3×20 mL), then dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by Biotage Flash 40S chromatography, eluting with 2:1 ethyl acetate-hexanes, to provide 3-(1-phenyl-ethylamino)-7-aza-bicyclo[2.2.1]heptane-2,7-dicarboxylic acid 7-tert-butyl ester 2-methyl ester as a 3:1 mixture of diastereomers (0.28 g, 93%). MS: 375 (M+H)+.

Workup

washThe organic layer was washed with brine (3×20 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by Biotage Flash 40S chromatography
washeluting with 2:1 ethyl acetate-hexanes

Sources & evidence

ORD record: ord-8376beffad3c420ba3b7f3aba2dd153e
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595327B2

Reaction notes

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