Triphenylphosphine → 1-(S)-(3-((7-chloro-2-quinolinyl)methoxy)phenyl)-3-(2-(2-(2-tetrahydropyranyloxy)-2-propyl)phenyl)propanol

HRID 258482Notes

Reaction equation

N(C(OCC)=O)=NC(OCC)=O.[Cl:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][C:20]([CH2:24][O:25][C:26]3[CH:27]=[C:28]([C@H:32]([OH:51])[CH2:33][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[C:41]([O:44][CH:45]4[CH2:50][CH2:49][CH2:48][CH2:47][O:46]4)([CH3:43])[CH3:42])[CH:29]=[CH:30][CH:31]=3)=[N:21]2)=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Cl:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][C:20]([CH2:24][O:25][C:26]3[CH:27]=[C:28]([C@@H:32]([OH:51])[CH2:33][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[C:41]([O:44][CH:45]4[CH2:50][CH2:49][CH2:48][CH2:47][O:46]4)([CH3:43])[CH3:42])[CH:29]=[CH:30][CH:31]=3)=[N:21]2)=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

At 0° C., diethyl azodicarboxylate (7.6 mL, 48.3 mmol) was added dropwise to a solution of the alcohol of Step 8 (17.47 g, 31.97 mmol), triphenylphosphine (12.60 g, 48.04 mmol) and R-(-)-α-methoxyphenylacetic acid (8.07 g, 48.6 mmol) in 320 mL of anhydrous THF. The mixture was stirred at 0° C. for 30 min and the solvents were evaporated. Flash chromatography of the residue on silica using EtOAc:toluene 2.5:97.5, 5:95 and 7.5:92.5 afforded 21.84 g (98%) of the inverted alcohol as the mandelate ester. [α]D -6.02° (c 1.99, THF). This ester was hydrolyzed to the title alcohol as in Example 1, Method B, Step 8.

Workup

customthe solvents were evaporated

Sources & evidence

ORD record: ord-482f499507434180b8eb50ad977b0704
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05266568

Reaction notes

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