Phenol → HCID 131733443, compound

Participants

Role	Name	HCID	Charge
Reactant	Phenol	HCID 996	—
Reactant	Toluene-4-sulfonic acid Chroman-3-ylmethyl ester	HCID 11267124	—
Reactant	(R)-tert-butyl 3-hydroxy-3-(3-hydroxyphenyl)propylcarbamate	HCID 90405310	—
Product	HCID 131733443	HCID 131733443	—

Reaction Steps

Alkylation of phenol (7, Intermediate I) with chroman-3-ylmethyl 4-methylbenzenesulfonate following the method used in Example 12 gave tert-butyl ((3R)-3-(3-(chroman-3-ylmethoxy)phenyl)-3-hydroxypropyl)carbamate as a colorless oil. Yield (71%); 1H NMR (400 MHz, DMSO-d6) δ 7.21 (t, J=7.6 Hz, 1H), 7.10-7.05 (m, 2H), 6.91 (s, 1H), 6.88 (d, J=7.6 Hz, 1H), 6.85-6.83 (m, 1H), 6.81-6.79 (m, 1H), 6.75 (d, J=8.4 Hz, 1H), 5.19 (d, J=4.8 Hz, 1H), 4.53-4.48 (m, 1H), 4.31-4.28 (m, 1H), 3.99-3.91 (m, 2H), 2.98-2.93 (m, 2H), 2.92-2.90 (m, 1H), 2.71-2.69 (m, 2H), 1.66 (q, J=6.8 Hz, 2H), 1.36 (s, 9H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09133154B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-41d3e2f27cc84e85b4cbde620b42cd53
Source note	uspto-grants-2015_09