HCID 178476812, compound → HCID 178476815, compound

HRID 1062531Notes

Reaction equation

HRID 1062531 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH2:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][PH:18](=[O:22])[O:19][CH2:20][CH3:21])=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pt]=O>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][CH2:16][CH2:17][PH:18](=[O:22])[O:19][CH2:20][CH3:21])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 178476812HCID 178476812, compound

Product 1

HCID 178476815HCID 178476815, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A solution of (±)-ethyl [3-(t-butyloxycarbonyl)aminocyclopentenyl]butylphosphinate (13) (2.95 g, 8.90 mmol) in methanol (30 cm3) was hydrogenated over platinum oxide (50 mg) at 40 psi for 3 hours. The catalyst was removed by filtration through celite and then washed with methanol (3×30 cm3). The solvent was removed in vacuo to yield the desired title compound (14) in quantitative yield (>90% cis isomer by NMR spectroscopy) as a colourless oil, which was used in the next step without further purification (2.14 g, 72%) (data for cis isomer only is reported): 1H-NMR (300 MHz, CDCl3) δH 0.93 (3H, 2×d, J=6.9 and 7.2 Hz, PCH2CH2CH2CH3),1.21-2.32 (25H, m, C(1)—H, C(2)—H, C(2)—H′, C(4)—H, C(4)—H′, C(5)—H and C(5)—H′, POCH2CH3, PCH2CH2CH2CH3, PCH2CH2CH2CH3, PCH2CH2CH2CH3, C(CH3)3), 4.13 (4H, m, OCH2CH3, C(3)—NH, C(3)—H); 13C-NMR (75 MHz, CDCl3) δC13.49 (s, PCH2CH2CH2CH3), 16.65 (d, 3JPOCC=3.98 Hz, POCH2CH3), 23.61 (s, C(5)), 23.85 (s, PCH2CH2CH2CH3), 23.88 and 24.04 (d, 3JPC=12.53 Hz, PCH2CH2CH2CH3),26.34 and 27.50 (2×d, JPC=87.08 and 87.38 Hz, PCH2CH2CH2CH3),28.38 (s, C(CH3)3), 33.02 (s, C(2)), 33.50 and 33.63 (2×d, 3JPC=9.08 and 9.98 Hz, C(4)), 34.24 and 35.50 (2×d, JPC=94.43 and 94.73 Hz, C(1)), 52.25 (m, C(CH3)3), 60.45 and 60.54 (d, 2JPOC=6.83 Hz, POCH2CH3), 78.79 and 79.11 (d, 3JPC=24.15 Hz, C(3)), 155.42 (s, C═O); 31P-NMR (121 MHz, CDCl3) δP 59.85 and 60.99; MS (CI, CH4) m/z 334.0 (12%) (MH+), 234.2 (100), 278.2 (23), 362.2 (16). Synthesis of (±)-cis-(3-aminocyclopentanyl)butylphosphinic acid (15)

Workup

  1. customThe catalyst was removed by filtration through celite
  2. washwashed with methanol (3×30 cm3)
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-309eab7339714aa382e537edd1b0a13c
Source dataset
uspto-grants-2005_11
Patent number
US06962907B2

Reaction notes

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