4-(4-Fluoro-benzyl)-piperidine → HCID 54284239, compound

HRID 970400Notes

Reaction equation

HRID 970400 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10](C=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:19][CH:18]=1.[C:30](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[CH2:30][N:27]1[CH2:26][CH2:25][CH:24]([CH2:23][C:20]2[CH:19]=[CH:18][C:17]([F:16])=[CH:22][CH:21]=2)[CH2:29][CH2:28]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 36998414-(4-Fluoro-benzyl)-piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 99644481-Boc-piperidine-3-carboxaldehyde

Product 1

HCID 54284239HCID 54284239, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (+/−)-N-(t-butoxycarbonyl)-3-piperidinecarboxaldehyde (521 mg, 2.45 mmol) and 4-(4-flourophenylmethyl)piperidine (315 mg, 1.63 mmol) in dry CH2Cl2 (20 mL) was stirred for 15 min when sodium triacetoxyborohydride (691 mg, 3.26 mmol, Aldrich) was added. The reaction was stirred for 4 h and then quenched with 10% NaOH (10 mL) and CH2Cl2 (100 mL). The organic layer was separated, dried over MgSO4, and conc. in vacuo to a pale yellow oil. The oil was purified by radial chromatography (SiO2, CH2Cl2:MeOH, 98:2) to yield 580 mg the product as a colorless oil. MS (ESI) 391 (M+H).

Workup

  1. additionwas added
  2. customquenched with 10% NaOH (10 mL) and CH2Cl2 (100 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. customThe oil was purified by radial chromatography (SiO2, CH2Cl2:MeOH, 98:2)

Sources & evidence

ORD record
ord-0bee50bbb1a041c8a305de69ce3fc61b
Source dataset
uspto-grants-2007_12
Patent number
US07312222B2

Reaction notes

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