Tetrabutylammonium Fluoride → HCID 178460559, compound

HRID 1062537Notes

Reaction equation

HRID 1062537 reaction equation
[Si]([O:8][C@@H:9]1[CH2:13][CH2:12][C@H:11]([CH2:14][PH:15](=[O:20])[O:16][CH:17]([CH3:19])[CH3:18])[CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH: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

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178460560HCID 178460560, compound

Product 1

HCID 178460559HCID 178460559, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (±)-cis-isopropyl [3t-butyldimethylsilyloxy)cyclopentanyl]methylphosphinate (5) (3.2 g, 10 mmol) in anhydrous THF (30 cm3) was added tetrabutylammonium fluoride (11 cm3 of a 1 M solution in THF). The reaction mixture was stirred at room temperature for 12 h at which time the solvent was removed in vacuo. The crude product was purified by short column vacuum chromatography on silica gel (15% ethanol/ethyl acetate); earlier fractions contained the trans isomer, later fractions contained the desired cis (6) isomer which was isolated as a colourless oil (1.8 g, 87%): 1H NMR (300 MHz, CDCl3) δ 1.28 and 1.31 (6H, d, J=6.3 and 6.3 Hz, OCHCH3), 1.45 (3H, d, J=113.2 Hz, PCH3), 1.61-2.32 (6H, m, C(1)—H, C(2)—H, C(2)—H′, C(4)—H, C(4)—H′ and C(5)—H), 4.26 (1H, m, C(3)—H), 4.61 (1H, m, OCHCH3), 13C NMR (75.46 MHz, CDCl3) δ 12.15 and 12.76 (PCH3, d, JPC=90.2 and 89.9 Hz), 23.62 (C(5)), 24.20 and 24.24 (POCCH3, 2×d, 3JPOCC=3.3 Hz), 35.24 and 35.29 (C(2, s), 35.81 and 35.89 (C(1), d, JPC=97.9 and 98.5 Hz), 35.98 and 36.01 (C(4), d, 3JPC=7.2 and 7.5 Hz), 69.11 and 69.12 (POCHCH3, d, 2JPOC=6.9 and 6.9 Hz), 72.8 and 73.3 (C(3), d, 3JPC=4.1 and 4.9 Hz), 31 P NMR (121 MHz, CDCl3) δ 59.4, 59.7, (ESI) 207.1154 (MH+-C9H20O3P requires 207.1150).

Workup

  1. customwas removed in vacuo
  2. customThe crude product was purified by short column vacuum chromatography on silica gel (15% ethanol/ethyl acetate)

Sources & evidence

ORD record
ord-5a80f259fe694ac882d85fe9f97c760f
Source dataset
uspto-grants-2005_11
Patent number
US06962907B2

Reaction notes

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