(4S)-4-Benzyl-5,5-diphenyl-1,3-oxazolidin-2-one → (S)-(-)-1-Benzyl-2,2-diphenylethylamine

HRID 1246379Notes

Reaction equation

HRID 1246379 reaction equation
[CH2:1]([C@H:8]1[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)OC(=O)[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CO.CC(O)=O.[Pd]>[NH2:9][C@@H:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:12]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 9818858(4S)-4-Benzyl-5,5-diphenyl-1,3-oxazolidin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 9925949(S)-(-)-1-Benzyl-2,2-diphenylethylamineYield 71.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

A solution of (S)-4-benzyl-5,5-diphenyl-2-oxazolidinone (7) (940 mg, 2.85 mmol) in MeOH/AcOH and a 10% Pd (121 mg, 1.14 mmol) on activated carbon was shaken for 43 h under 4–5 atm pressure of hydrogen at room temperature. The catalyst was filtered off over Hyflo Super Cell and organic solvents were evaporated under reduced pressure. The resulting residue was treated with HCl, stirred for 2 h at room temperature, made basic with NaOH pellets, and saturated with K2CO3 and NaCl. Organics were then extracted into dichloromethane (4×50 ml), dried over MgSO4/K2CO3 and concentrated under reduced pressure to obtain a crude product. Purification over silica gel, eluting with a 3:7 and 4:6 mixture of AcOEt and petroleum ether, gave the title compound (8) (584 mg, 71%) as a light-brown solid. m.p. 71–72° C. [α]D25=−8.03° (c, 0.1046 in CHCl3). δH 1.21 (2H, broad s, NH2), 2.29 (1H, dd, 3J=9.6 Hz, 2J=13.5 Hz, CH2—Ph), 2.79 (1H, dd, 3J=2.1 Hz, 2J=13.2 Hz, CH2—Ph), 3.71 (1H, d, 3J=9.9 Hz, CH—Ph2), 3.81 (1H, ddd, 3J=2.7, 9.9 and 12.6 Hz, CH—NH2), 7.06–7.33 (15H, m, Ar—H), δC 41.9 (CH2—Ph), 55.7 and 59.7 (CH—Ph2 and CH—NH2), 126.3, 126.5, 126.6, 128.1, 128.2, 128.4, 128.7, 128.8 and 129.1 (o-, m- and p-Ar), 139.7, 142.6 and 143.1 (α-Ar). ir 3387 (NH2). m/e (CI—NH3) 288 (MH+, 100%).

Workup

  1. filtrationThe catalyst was filtered off over Hyflo Super Cell and organic solvents
  2. customwere evaporated under reduced pressure
  3. additionThe resulting residue was treated with HCl
  4. extractionOrganics were then extracted into dichloromethane (4×50 ml)
  5. dry with materialdried over MgSO4/K2CO3
  6. concentrationconcentrated under reduced pressure
  7. customto obtain a crude product
  8. customPurification over silica gel
  9. washeluting with a 3:7 and 4:6 mixture of AcOEt and petroleum ether

Sources & evidence

ORD record
ord-6831b0739a1c4c45ac1f4ff30099161a
Source dataset
uspto-grants-2006_10
Patent number
US07126028B1

Reaction notes

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