Triphenylphosphine → Thiocholesterol

HRID 20900Notes

Reaction equation

HRID 20900 reaction equation
OC1CN[C@H](CO)C1.[CH3:9][CH:10]([CH2:12][CH2:13][CH2:14][C@H:15]([C@@H:17]1[C@:35]2([CH3:36])[C@H:20]([C@H:21]3[C@H:32]([CH2:33][CH2:34]2)[C@:30]2([CH3:31])[C:24]([CH2:25][C@H:26]([CH2:28][CH2:29]2)[SH:27])=[CH:23][CH2:22]3)[CH2:19][CH2:18]1)[CH3:16])[CH3:11].C([O-])(=O)CCC([O-])=O.[N+](C1C=CC(SSC2C=CC([N+]([O-])=O)=CN=2)=NC=1)([O-])=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClC(Cl)C.CN(C1C=CN=CC=1)C.C(#N)C.ClC(Cl)C.C(#N)C>[CH3:11][CH:10]([CH2:12][CH2:13][CH2:14][C@H:15]([C@@H:17]1[C@:35]2([CH3:36])[C@H:20]([C@H:21]3[C@H:32]([CH2:33][CH2:34]2)[C@:30]2([CH3:31])[C:24]([CH2:25][C@H:26]([CH2:28][CH2:29]2)[SH:27])=[CH:23][CH2:22]3)[CH2:19][CH2:18]1)[CH3:16])[CH3:9]

Participants

8

Reactant 3

HCID 11776TriphenylphosphineHCID 164742,2'-Dithiobis(5-nitropyridine)HCID 865981504-Hydroxy-L-prolinol thiocholesterol succinate

Product 1

HCID 65075Thiocholesterol

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolventHCID 63651,1-DichloroethaneSolventHCID 21218066Acetonitrile dichloroethaneSolvent

Procedure

Succinate 27 (2.1 g, 1.9 mmol) was dissolved in dichloroethane (8 mL). To that solution DMAP (0.228 g, 1.9 mmol) was added. 2,2′-Dithio-bis(5-nitropyridine) (0.58 g, 1.9 mmol) in acetonitrile/dichloroethane (3:1, 8 mL) was added successively. To the resulting solution triphenylphosphine (0.49 g, 1.9 mmol) in acetonitrile (4 ml) was added. The reaction mixture turned bright orange in color. The solution was agitated briefly using wrist-action shaker (5 mins). Long chain alkyl amine-CPG (LCAA-CPG) (12 g, 1860 μmoles, 155 μm/g) was added. The suspension was agitated for 4 h. The CPG was filtered through a sintered funnel and washed with acetonitrile, dichloromethane and ether successively. Unreacted amino groups were masked using acetic anhydride/pyridine. The loading capacity of the CPG 28 was measured by taking UV measurement. (57 μM/g).

Workup

  1. customwrist-action shaker (5 mins)
  2. stirringThe suspension was agitated for 4 h
  3. filtrationThe CPG was filtered through a sintered funnel
  4. washwashed with acetonitrile, dichloromethane and ether successively

Sources & evidence

ORD record
ord-587e268d3f7243d5b5a6d66f01dde962
Source dataset
uspto-grants-2010_06
Patent number
US07745608B2

Reaction notes

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