Acetic Acid → (3-Chloro-5-diethylaminomethyl-2-fluoro-benzyl)-carbamic acid tert-butyl ester

HRID 1527489Notes

Reaction equation

HRID 1527489 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([CH:15]=O)[CH:12]=[C:11]([Cl:17])[C:10]=1[F:18])([CH3:4])([CH3:3])[CH3:2].[CH2:20]([NH:22][CH2:23][CH3:24])[CH3:21].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([CH2:15][N:22]([CH2:23][CH3:24])[CH2:20][CH3:21])[CH:12]=[C:11]([Cl:17])[C:10]=1[F:18])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8021DiethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86673866HCID 86673866, compound

Product 1

HCID 68283941(3-Chloro-5-diethylaminomethyl-2-fluoro-benzyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3-chloro-2-fluoro-5-formyl-benzyl)-carbamic acid tert-butyl ester (200 mg, 0.7 mmol), diethylamine (51 mg, 0.7 mmol) and acetic acid (0.06 mL) in THF (mL) was stirred for 30 min at ambient temperature. After addition of sodium triacetoxyborohydride (368 mg, 1.7 mmol) the reaction was stirred overnight, quenched by addition of saturated aqueous NaHCO3 and extracted with EtOAc. The solvent was removed in vacuo and the residue was purified by RP-preparative HPLC (Waters Sunfire, C18-ODB, 5 μm, 30×100 mm, 5-100% CH3CN/H2O/20 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 40 mL/min) to give the title compound. MS (LC-MS): 345.0 [M]+; tR (HPLC conditions c): 4.09 min.

Workup

  1. customquenched by addition of saturated aqueous NaHCO3
  2. extractionextracted with EtOAc
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by RP-preparative HPLC (Waters Sunfire, C18-ODB, 5 μm, 30×100 mm, 5-100% CH3CN/H2O/20 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 40 mL/min)

Sources & evidence

ORD record
ord-e5547d1747af4be6a9f6e0ba9417a5a5
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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