Water → (1S,3S,5S)-3-(b enzylamino-methyl)-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

Benzylamine (17.5 mmol, 1.0 eq) is added to a solution of (1S,3S,5S)-3-formyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester (17.5 mmol, 1.0 eq) in DCM (100 mL). The mixture is treated with sodium triacetoxyborohydride (24.5 mmol, 1.4 eq), stirred for additional 14 h, poured into water (200 mL) and stirred vigorously for 10 min. The layers are separated and the aqueous layer is extracted twice with DCM (2×100 mL). The combined organic layers are washed with sat. NaHCO3 solution (100 mL) and water (100 mL), dried over Na2SO4 and concentrated in vacuo to give the desired benzylamine as a brownish oil which is used without further purification. LC-MS (basic): tR=0.96 min; [M+H]+=303.3.

1. stirringstirred vigorously for 10 min
2. customThe layers are separated
3. extractionthe aqueous layer is extracted twice with DCM (2×100 mL)
4. washThe combined organic layers are washed with sat. NaHCO3 solution (100 mL) and water (100 mL)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated in vacuo

ORDレコード

ord-378be2f95ef447ad8390514674027f9f

出典データセット

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08288435B2