Benzylamine → HCID 59444329, compound

HRID 560337Notes

Reaction equation

HRID 560337 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:13][C:14]([N:16]1[CH2:21][C@H:20]2[C@H:18]([CH2:19]2)[C@H:17]1[CH:22]=O)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[C:9]([O:13][C:14]([N:16]1[CH2:21][C@H:20]2[C@H:18]([CH2:19]2)[C@H:17]1[CH2:22][NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59444332(1S,2S,5R)-2-Formyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic Acid Tert-butyl Ester

Product 1

HCID 59444329HCID 59444329, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3ee3750631e942fc9965bc93aac5992d
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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