Benzylamine → (1S,2S,5R)-2-(Benzylamino-methyl)-3-aza-bicyclo[3.1.0]hexane-3-carboxylic Acid Tert-butyl Ester

Benzylamine (2.95 mmol, 1.2 eq) is added to a solution of (1S,2S,5R)-2-Formyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (2.46 mmol, 1.0 eq) in chloroform (6.0 mL). After 10 min the mixture is treated with sodium triacetoxyborohydride (2.95 mmol), stirred for additional 15 h and poured into a sat. aq. NaHCO3 solution. The layers are separated and the aq. layer is extracted once with chloroform. The combined organic layers are washed twice with sat. NaHCO3 solution and water. The solvents are removed in vacuo and the residue is dissolved in ether (30 mL). Aq. HCl (0.1 M, 40 mL) is added, the layers are separated and the organic layer is extracted twice with aq. HCl (0.1 M, 30 mL each). The combined aq. layers are washed with ether (20 mL), made alkaline by addition of NaOH solution (1.0 M, 20 mL) and extracted three times with ether (40 mL each). The combined organic layers are dried over MgSO4 and concentrated in vacuo to give a crude product which is used without further purification. LC-MS (basic): tR=0.96 min; [M+H]+=303.3.

1. customThe layers are separated
2. extractionthe aq. layer is extracted once with chloroform
3. washThe combined organic layers are washed twice with sat. NaHCO3 solution and water
4. customThe solvents are removed in vacuo
5. dissolutionthe residue is dissolved in ether (30 mL)
6. additionAq. HCl (0.1 M, 40 mL) is added
7. customthe layers are separated
8. extractionthe organic layer is extracted twice with aq. HCl (0.1 M, 30 mL each)
9. washThe combined aq. layers are washed with ether (20 mL)
10. additionby addition of NaOH solution (1.0 M, 20 mL)
11. extractionextracted three times with ether (40 mL each)
12. dry with materialThe combined organic layers are dried over MgSO4
13. concentrationconcentrated in vacuo

ORDレコード

ord-3ee3750631e942fc9965bc93aac5992d

出典データセット

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08063099B2