Reaktion #314359

Reaktionsgleichung

compound 13

(11S,11aS)-8-Benzyloxy-10-(tert-butyloxycarbonyl)-7-methoxy-11-(tetrahydroxy-pyran-2-yloxy)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5-one

Psi

→

phenol

Ausbeute 90.0%

(11S,11aS)-8-Hydroxy-10-(tert-butyloxycarbonyl)-7-methoxy-11-(tetrahydroxy-pyran-2-yloxy)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5-one

Ausbeute 90.0%

Lösungsmittel

—

alcohol

EtOAc hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationwas filtered through Celite, and removal of excess solvent under reduced pressure

Vorschrift

A catalytic amount of 10% palladium on carbon (380 mg) was added to a solution of THP protected compound 13 (3.8 g, 7 mmol) in absolute alcohol (30 mL). The reaction mixture was hydrogenated for 3 h at 35 Psi. When the reaction was complete as indicated by TLC (SiO2, 50% EtOAc-hexane) the reaction mixture was filtered through Celite, and removal of excess solvent under reduced pressure afforded the phenol 14 (2.8 g, 6.25 mmol, 90% yield, mixture of diastereomers from THP protecting group) as a white solid: [α]20D=+84° (c=0.48, CHCl31H NMR (CDCl3, 400 MHz): δ 1.35 (s, 18H, Boc), 1.48-1.68 (m, 6H, THP), 1.69-1.88 (m, 6H, THP), 1.91-2.18 (m, 8H, 1-H, 2-H), 3.44-3.75 (m, 8H, 3-H, 11a-H, THP), 3.84-4.02 (m, 8H, 7-OMe, THP), 4.96-5.09 (m, 1H, THP), 5.10-5.18 (m, 1H, THP), 5.69-5.76 (d, 1H, 11-H), 5.77-5.87 (d, 1H, 11-H), 6.03 (s, 1H, OH), 6.14 (s, 1H, OH), 6.49 (s, 1H, 9-H), 6.86 (s, 1H, 9-H), 7.28 (s, 1H, 6-H), 7.32 (s, 1H, 6-H); 13C NMR (CDCl3, 400 MHz): δ 19.9, 20.7, 23.1, 23.2, 25.1, 25.3, 28.0, 28.1, 28.9, 29.1, 30.8, 31.2, 46.3, 56.13, 56.19, 60.0, 60.2, 63.4, 64.5, 81.0, 81.1, 87.9, 91.1, 95.8, 100.7, 109.6, 110.0, 116.4, 117.0, 125.5, 125.9, 130.2, 130.5, 145.7, 145.8, 147.4, 147.5, 154.9, 155.3, 167.4, 167.6; IR (neat): 3266, 2947, 1703, 1631, 1612, 1514, 1468, 1411, 1368, 1331, 1275, 1201, 1163, 1116, 1023 cm−1; MS (FAB) m/z (relative intensity) 471 ([M+Na]+., 15), 449 (M+., 99), 246 (100), 347 (25).

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