Dichloromethane → tert-Butyl 4-((4-fluorobenzylamino)methyl)benzylcarbamate

HRID 1889664Notes

Reaction equation

HRID 1889664 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.C(Cl)Cl.[NH2:13][CH2:14][C:15]1[CH:29]=[CH:28][C:18]([CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:17][CH:16]=1.[BH4-].[Na+]>CC(O)C>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:13][CH2:14][C:15]2[CH:29]=[CH:28][C:18]([CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[CH:17][CH:16]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 680234-FluorobenzaldehydeHCID 3354775tert-butyl N-{[4-(aminomethyl)phenyl]methyl}carbamateHCID 4311764Sodium borohydride

Product 1

HCID 66616762tert-Butyl 4-((4-fluorobenzylamino)methyl)benzylcarbamateYield 50.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 4-fluorobenzaldehyde (496 mg, 4.00 mmol) in a mixed solvent of CH2Cl2 (10 mL) and 2-propanol (2 mL) at rt was added tert-butyl 4-(aminomethyl)benzylcarbamate (945 mg, 4.00 mmol, Aldrich). The reaction mixture was stirred at rt overnight. The next morning, sodium borohydride (296 mg, 8.0 mmol) was added, and the mixture was stirred at rt for 2 h. The reaction mixture was quenched by adding 3 mL of MeOH and 3 mL of saturated aq NaHCO3. The mixture was extracted with EtOAc (3×50 mL). The combined organic extracts were dried, concentrated and purified by flash column chromatography on silica gel eluting with CH2Cl2/EtOAc to give the title compound (0.69 g, 48%) as a viscous material. MS (ESI): 345.1 (M+H)+.

Workup

  1. stirringthe mixture was stirred at rt for 2 h
  2. customThe reaction mixture was quenched
  3. additionby adding 3 mL of MeOH and 3 mL of saturated aq NaHCO3
  4. extractionThe mixture was extracted with EtOAc (3×50 mL)
  5. customThe combined organic extracts were dried
  6. concentrationconcentrated
  7. custompurified by flash column chromatography on silica gel eluting with CH2Cl2/EtOAc

Sources & evidence

ORD record
ord-2e54c2e4e57942c2af608bf31b6a189f
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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