Benzylamine → HCID 66703722, compound

HRID 425792Notes

Reaction equation

HRID 425792 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[CH2:23][C@H:22]2[C@H:18]([CH2:19][CH2:20][CH2:21]2)[C@H:17]1[CH:24]=O)=[O:15])([CH3:12])([CH3:11])[CH3:10].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CC(=O)OCC.CCCCCCC>[C:9]([O:13][C:14]([N:16]1[CH2:23][C@H:22]2[C@H:18]([CH2:19][CH2:20][CH2:21]2)[C@H:17]1[CH2:24][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

7

Reactant 4

HCID 7504BenzylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86643541HCID 86643541, compound

Product 1

HCID 66703722HCID 66703722, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

Benzylamine (0.263 mL, 1.75 eq) was added to a solution of (1S,2S,5R)-2-formyl-3-aza-bicyclo[3.3.0]-octane-3-carboxylic acid tert.-butyl ester (330 mg, 1 eq) in chloroform (10 mL). After 15 min the mixture was treated with NaBH(OAc)3 (292.25 mg, 1 eq), stirred for 2 h and poured into a sat. aq NaHCO3 solution. The layers were separated and the aqueous layer was extracted twice with chloroform. The combined org. extracts were washed with sat. NaHCO3 solution, dried over anh. MgSO4, filtered and concentrated in vacuo to give a crude yellow oil. FC (EA/n-heptane: 3/7 to 7/3) gave the title compound as a colourless oil

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted twice with chloroform
  3. washextracts were washed with sat. NaHCO3 solution
  4. dry with materialdried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a crude yellow oil

Sources & evidence

ORD record
ord-23babfbaecd2453b8807e432eca52ee2
Source dataset
uspto-grants-2012_01
Patent number
US08106215B2

Reaction notes

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