(2S,4S)-tert-butyl-4-(diphenylphosphino)-2-(diphenylphosphino)-2-(diphenylphosphinomethyl)-1-pyrrolidinecarboxylate → (S)-1-[2-(tert-Butoxycarbonyl)-3-(2-methoxyethoxy)propyl]-1-cyclopentanecarboxylic acid

HRID 53456Notes

Reaction equation

HRID 53456 reaction equation
C1(N)CCCCC1.[C:8]([O:12][C:13](/[C:15](/[CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])=[CH:16]/[C:17]1([C:22]([OH:24])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].C(OC(N1C[C@@H](P(C2C=CC=CC=2)C2C=CC=CC=2)C[C@]1(P(C1C=CC=CC=1)C1C=CC=CC=1)CP(C1C=CC=CC=1)C1C=CC=CC=1)=O)(C)(C)C>C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Rh].[Rh]>[C:8]([O:12][C:13]([C@H:15]([CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])[CH2:16][C:17]1([C:22]([OH:24])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:14])([CH3:10])([CH3:9])[CH3:11]

Participants

4

Reactant 2

HCID 57318003(2S,4S)-tert-butyl-4-(diphenylphosphino)-2-(diphenylphosphino)-2-(diphenylphosphinomethyl)-1-pyrrolidinecarboxylateHCID 67726576(E)-1-[2-(tert-butoxycarbonyl)-3-(2-methoxyethoxy)prop-1-enyl]-1-cyclopentanecarboxylic acid cyclohexylamine salt

Product 1

HCID 11810308(S)-1-[2-(tert-Butoxycarbonyl)-3-(2-methoxyethoxy)propyl]-1-cyclopentanecarboxylic acidYield 100.4%

Reagents, catalysts & solvents 1

HCID 6436379Rhodium, di-mu-chlorobis((1,2,5,6-eta)-1,5-cyclooctadiene)di-Catalyst

Procedure

(E)-1-[2-(tert-Butoxycarbonyl)-3-(2-methoxyethoxy)prop-1-enyl]-1-cyclopentanecarboxylic acid cyclohexylamine salt (100 mg, 0.22 mmole), chloro(1,5-cyclooctadiene)rhodium(I)dimer (3.0 mg, 0.0006 mmole) and (2S,4S)-tert-butyl-4-(diphenylphosphino)-2-(diphenylphosphino)-2-(diphenylphosphinomethyl)-1-pyrrolidinecarboxylate (7.6 mg, 0.013 mmole) were charged to a glass vial and the top sealed with a rubber septum. The system was purged with argon, methanol (2.5 mL) was added and the mixture purged with argon for 30 minutes. The reaction was hydrogenated at 104 kPa (15 p.s.i.) and room temperature for 20.5 hours. The reaction mixture was purged with nitrogen, Dowex 50W-X2 ion exchange resin (200 mesh, 100 mg) added and the mixture stirred for 15 minutes. The ion exchange resin was removed by filtration and the methanol removed by evaporation under reduced pressure to give the title compound as an oil (73 mg, quantitative) (ratio S:R 61:39), Rf =0.3 (ethyl acetate/hexane, 1:1+1% acetic acid).

Workup

  1. customthe top sealed with a rubber septum
  2. customThe system was purged with argon, methanol (2.5 mL)
  3. additionwas added
  4. customthe mixture purged with argon for 30 minutes
  5. customThe reaction mixture was purged with nitrogen, Dowex 50W-X2 ion exchange resin (200 mesh, 100 mg)
  6. additionadded
  7. customThe ion exchange resin was removed by filtration
  8. customthe methanol removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-415550403aa0416e8ab21d95cc28c3e6
Source dataset
uspto-grants-1997_04
Patent number
US05618970

Reaction notes

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