Piperidine → (R)-1-((5-azido-5,6,7,8-tetrahydronaphthalen-2-yl)methyl)piperidine

HRID 1431992Notes

Reaction equation

HRID 1431992 reaction equation
[N:1]([C@@H:4]1[CH2:13][CH2:12][CH2:11][C:10]2[CH:9]=[C:8]([CH:14]=O)[CH:7]=[CH:6][C:5]1=2)=[N+:2]=[N-:3].[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(OC)(OC)OC.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CC(O)=O.C(Cl)Cl>[N:1]([C@@H:4]1[CH2:13][CH2:12][CH2:11][C:10]2[CH:9]=[C:8]([CH2:14][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH:7]=[CH:6][C:5]1=2)=[N+:2]=[N-:3]

Participants

7

Reactant 4

HCID 8082PiperidineHCID 9005Trimethyl orthoformateHCID 5049666Sodium triacetoxyborohydrideHCID 59771822(R)-5-azido-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde

Product 1

HCID 86604857(R)-1-((5-azido-5,6,7,8-tetrahydronaphthalen-2-yl)methyl)piperidine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 100 mL flame dry round bottom flask was added (R)-5-azido-5,6,7,8-tetrahydro-naphthalene-2-carbaldehyde (200 mg, 0.99 mmol), piperidine (0.5 mL, 5 mmol), dry DCM (10 mL), HOAc (1 drop), and CH(OMe)3. The resulting mixture was stirred under N2 for 3 h at RT. Then, NaBH(OAc)3 (632 mg, 2.98 mmol) was added and stirred for 20 h. The reaction mixture was quenched with 5% NaHCO3 and concentrated in vacuo. The residue was partitioned between EtOAc and H2O. The organic layer was washed with H2O, brine, dried over MgSO4 and concentrated. The residue was purified by SiO2 (95% DCM:5% MeOH) to afford the title compound. MS (m/z): 271.2 (M+H) (Calc'd. for C16H22N4:270.37).

Workup

  1. temperatureTo a 100 mL flame
  2. customdry round bottom flask
  3. stirringstirred for 20 h
  4. customThe reaction mixture was quenched with 5% NaHCO3
  5. concentrationconcentrated in vacuo
  6. customThe residue was partitioned between EtOAc and H2O
  7. washThe organic layer was washed with H2O, brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customThe residue was purified by SiO2 (95% DCM:5% MeOH)

Sources & evidence

ORD record
ord-e852cfd629a842d19b4d315d068b2038
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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