4-(4-Fluoro-benzyl)-piperidine → HCID 23509661, compound

HRID 970403Notes

Reaction equation

HRID 970403 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH:13]([CH:16]=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:21][CH:20]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[F:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][CH:26]2[CH2:27][CH2:28][N:29]([CH2:16][CH:13]3[CH2:14][CH2:15][N:11]([C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:10])[CH2:12]3)[CH2:30][CH2:31]2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 36998414-(4-Fluoro-benzyl)-piperidineHCID 4620242Benzyl 3-formylpyrrolidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 23509661HCID 23509661, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (+/−)-N-(benzyloxycarbonyl)-3-pyrrolidinecarboxaldehyde (416 mg, 1.79 mmol) and 4-(4-flourophenylmethyl)piperidine (518 mg, 2.69 mmol) in dry CH2Cl2 (15 mL) were stirred for 15 min when sodium triacetoxyborohydride (759 mg, 3.58 mmol, Aldrich) was added. The reaction was stirred for 2 h and then quenched with 1M aqueous HCl (50 mL) and CH2Cl2 (200 mL). The reaction was brought to pH 11 with 1M aqueous NaOH. The organic layer was separated, washed with brine, dried over MgSO4, and conc. in vacuo to a pale yellow oil. The oil was purified by radial chromatography (SiO2, CH2Cl2:MeOH, 97:3) to yield the product as a colorless oil. MS (ESI) 411 (M+H).

Workup

  1. additionwas added
  2. customquenched with 1M aqueous HCl (50 mL) and CH2Cl2 (200 mL)
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customThe oil was purified by radial chromatography (SiO2, CH2Cl2:MeOH, 97:3)

Sources & evidence

ORD record
ord-09613e9698de4d2c8fd091ec56c2c8ee
Source dataset
uspto-grants-2007_12
Patent number
US07312222B2

Reaction notes

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