Phenol → tert-butyl ((3R)-3-(3-((1,1-dioxidotetrahydro-2H-thiopyran-3-yl)methoxy)phenyl)-3-hydroxypropyl)carbamate

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Reaction Steps

Reaction between methyl 3-(bromomethyl)tetrahydro-2H-thiopyran 1,1-dioxide and phenol (7, Intermediate I) following the method used in Example 7 gave tert-butyl ((3R)-3-(3-((1,1-dioxidotetrahydro-2H-thiopyran-3-yl)methoxy)phenyl)-3-hydroxypropyl)carbamate as a light pink semi-solid. Yield (0.43 g, 65%); 1H NMR (400 MHz, CDCl3): δ 7.24 (t, J=8.0 Hz, 1H), 6.93 (d, J=8.0 Hz, 2H), 6.77-6.75 (m, 1H), 4.86 (bs, 1H), 4.72-4.70 (m, 1H), 3.95-3.92 (m, 1H), 3.90-3.88 (m, 1H), 3.38 (s, 1H), 3.26-3.22 (m, 1H), 3.18-3.13 (m, 1H), 3.06 (d, J=4.0 Hz 1H), 2.97-2.88 (m, 2H), 2.65 (bs, 1H), 2.20-2.04 (m, 2H), 1.99-1.95 (m, 1H), 1.84-1.81 (m, 2H), 1.45 (s, 9H). MS: m/z 414.43 [M+H]+.

Provenance & Evidence