Morpholine → 2-Methylhept-2-enoic acid

HRID 1650320Notes

Reaction equation

HRID 1650320 reaction equation
C(OC(N1CC(F)C[C@H]1C=C([C:16]1[CH2:22][C@H:21]2N([C:19](=O)[C@@H:20]2[C@H:23]([OH:25])C)[C:17]=1[C:27](OCC=C)=O)C)=O)C=C.N1CC[O:36]CC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:19][C:20]([C:23]([OH:36])=[O:25])=[CH:21][CH2:22][CH2:16][CH2:17][CH3:27]

Participants

7

Reactant 3

HCID 8083MorpholineHCID 11776TriphenylphosphineHCID 86743911allyl (5R,6S)-3-[2-{(2S)-1-allyloxycarbonyl-4-fluoropyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Product 1

HCID 534110972-Methylhept-2-enoic acid

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of allyl (5R,6S)-3-[2-{(2S)-1-allyloxycarbonyl-4-fluoropyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (1.7 g), morpholine (694 μl), and triphenylphosphine (199 mg) in tetrahydrofuran (30 ml) and ethanol (10 ml) was added tetrakis(triphenylphosphine)palladium(0) (263 mg) at room temperature. After stirring for an hour, the precipitate was filtered, washed in turn with dichloromethane (3 times) and acetone (twice), and dried under reduced pressure to give (5R,6S)-3-[2-{(2S)-4-fluoropyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1hydroxyethyl]-7-oxo-1-azabicyclo 3.2.0]hept-2-ene-2carboxylic acid (248 mg).

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed in turn with dichloromethane (3 times) and acetone (twice), and
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-7e4eaef3f42d41b68ddd38ec7d77cf53
Source dataset
uspto-grants-1990_05
Patent number
US04923857

Reaction notes

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