HCID 178460554, compound → HCID 178460558, compound

HRID 1062540Notes

Reaction equation

HRID 1062540 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH2:12][C:11]([CH2:14][PH:15](=[O:20])[O:16][CH:17]([CH3:19])[CH3:18])=[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][PH:15](=[O:20])[O:16][CH:17]([CH3:18])[CH3:19])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 178460554HCID 178460554, compound

Product 1

HCID 178460558HCID 178460558, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A solution of isopropyl (3-t-butyloxyaminocyclopentenyl)methylphosphinate (9) (3.4 g, 10.7 mmol) in methanol (30 cm3) was hydrogenated over platinum oxide (50 mg) at 40 psi for 3 h. The catalyst was removed by filtration through celite and then washed with methanol (3×30 cm3). The solvent was removed in vacuo and the crude product was purified by short column vacuum chromatography on silica gel (15% ethanol/ethyl acetate) to yield the desired cis isomer (10) as a colourless oil (2.1 g, 95%): 1H NMR (300 MHz, CDCl3) δ 1.24 (3H, 2×d, J=6.3 Hz, POCHCH3), 1.32 (3H, d, J=6.3 Hz, POCHCH3), 1.44 (9H, br. s, C(CH3)3), 1.48 and 1.49 (3H, d, J=14.7 and 14.1 Hz, PCH3), 1.58-1.75 (2H, m, C(2)—H, C(4)—H), 2.41-2.72 (5H, m, C(1)—H, C(2)—H′, C(4)—H′, C(5)—H and C(5)—H′), 4.53 (2H, m, POCHCH3 and NH), 4.84 (1H, br. m, C(3)—H),

Workup

  1. customThe catalyst was removed by filtration through celite
  2. washwashed with methanol (3×30 cm3)
  3. customThe solvent was removed in vacuo
  4. customthe crude product was purified by short column vacuum chromatography on silica gel (15% ethanol/ethyl acetate)

Sources & evidence

ORD record
ord-21b3e256deeb4573baa09f907fd7dd80
Source dataset
uspto-grants-2005_11
Patent number
US06962907B2

Reaction notes

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