Benzylamine → HCID 66844756, compound

HRID 2064482Notes

Reaction equation

HRID 2064482 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[C@H:23]([CH:24]=O)[CH2:22][C@H:21]2[C@@H:17]1[CH2:18][CH2:19][CH2:20]2)=[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(Cl)Cl.C(O)(=O)C>[C:9]([O:13][C:14]([N:16]1[C@H:23]([CH2:24][NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:22][C@H:21]2[C@@H:17]1[CH2:18][CH2:19][CH2:20]2)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

8

Reactant 4

HCID 7504BenzylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 58104590HCID 58104590, compound

Product 1

HCID 66844756HCID 66844756, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Benzylamine (2.76 mmol, 2.3 eq) is added to a solution of (1S,3S,5S)-3-formyl-2-azabicyclo[3.3.0]octane-2-carboxylic acid tert-butyl ester (1.2 mmol, 1.0 eq) in chloroform (10 mL). The mixture is stirred for 5 min, treated with sodium triacetoxyborohydride (4.8 mmol, 4.0 eq) and acetic acid (0.05 mL), stirred for additional 14 h and poured into sat. NaHCO3 solution. DCM is added, the layers are separated and the aqueous layer is extracted with DCM. The combined organic layers are washed with water (100 mL) and concentrated in vacuo. The residue is dissolved in ether and extracted three times with hydrochloric acid (0.1 M). The combined aqueous layers are extracted once with ether, made basic (pH 9-10) by addition of NaOH solution (1.0M) and extracted three times with ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo to give the desired benzylamine which is used without further purification. LC-MS: tR=0.89 min; [M+H]+=331.5.

Workup

  1. stirringstirred for additional 14 h
  2. customthe layers are separated
  3. extractionthe aqueous layer is extracted with DCM
  4. washThe combined organic layers are washed with water (100 mL)
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue is dissolved in ether
  7. extractionextracted three times with hydrochloric acid (0.1 M)
  8. extractionThe combined aqueous layers are extracted once with ether
  9. additionby addition of NaOH solution (1.0M)
  10. extractionextracted three times with ether
  11. dry with materialThe combined organic layers are dried over MgSO4
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-404e450ad62741d6a1614e1b28bc9a56
Source dataset
uspto-grants-2012_10
Patent number
US08288429B2

Reaction notes

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