Sodium Bicarbonate → Tert-butyl 1-(4-chloro-3-fluorobenzyl)-4-piperidinylcarbamate

HRID 1070511Notes

Reaction equation

HRID 1070511 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[F:10].[NH:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13][CH2:12]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:11]2[CH2:12][CH2:13][CH:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:15][CH2:16]2)=[CH:4][C:3]=1[F:10]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 7238334-(N-Boc-amino)piperidineHCID 27249854-Chloro-3-FluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 68886889Tert-butyl 1-(4-chloro-3-fluorobenzyl)-4-piperidinylcarbamateYield 105.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chloro-3-fluorobenzaldehyde (0.793 g) and tert-butyl 4-piperidinylcarbamate (1.00 g) were stirred under nitrogen in dried tetrahydrofuran (25 ml). Sodium triacetoxyborohydride (1.266 g) was then added and left for 24 hours. Saturated sodium hydrogen carbonate was added to the reaction, with the resulting solution being extracted three times with dichloromethane. The pooled organic phases were washed once with water, once with brine, dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to leave tert-butyl 1-(4-chloro-3-fluorobenzyl)-4-piperidinylcarbamate (1.80 g) as a white solid.

Workup

  1. extractionbeing extracted three times with dichloromethane
  2. washThe pooled organic phases were washed once with water, once with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-888ac7d47a8345c58d3c8ed3762539d4
Source dataset
uspto-grants-2005_06
Patent number
US06903085B1

Reaction notes

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