Acetic Acid → HCID 59568860, compound

HRID 1643292Notes

Reaction equation

HRID 1643292 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([O:20][CH3:21])[CH2:9][C@H:10]([CH2:15][CH2:16][CH2:17][CH:18]=O)[C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1.[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH2:28])=[CH:25][C:24]=1[CH3:31].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClCCCl>[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH:28][CH2:18][CH2:17][CH2:16][CH2:15][C@@H:10]([CH2:9][C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[O:20][CH3:21])[C:11]([O:13][CH3:14])=[O:12])=[CH:25][C:24]=1[CH3:31]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2774599(4-Fluoro-3-methylphenyl)methanamineHCID 5049666Sodium triacetoxyborohydrideHCID 59568821HCID 59568821, compound

Product 1

HCID 59568860HCID 59568860, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (S)-methyl 2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)-6-oxohexanoate (40 mg, 0.13 mmol) in 2 mL DCE was added 4-Fluoro-3-methyl-benzylamine (21 mg, 0.15 mmol) followed by NaBH(OAc)3 (39.9 mg, 1.4 mmol) and AcOH (9.3 mg, 9 μL, 0.15 mmol) at room temperature. The mixture was stirred for 8 h at the room temperature. The reaction was quenched by pouring into 10 mL 5% aqueous NaOH and diluted with ethyl acetate. The mixture was extracted with more ethyl acetate (3×20 mL) and the combined organic layers washed with brine (2×10 mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the crude product used directly in the next step without further purification.

Workup

  1. customThe reaction was quenched
  2. additionby pouring into 10 mL 5% aqueous NaOH
  3. additiondiluted with ethyl acetate
  4. extractionThe mixture was extracted with more ethyl acetate (3×20 mL)
  5. washthe combined organic layers washed with brine (2×10 mL)
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed under reduced pressure
  8. customthe crude product used directly in the next step without further purification

Sources & evidence

ORD record
ord-3b05146298ac4e82b4ce3e8df2581768
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

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