Phenol → HCID 131733443, compound

HRID 2277061Notes

Reaction equation

HRID 2277061 reaction equation
C1(O)C=CC=CC=1.[OH:8][C@@H:9]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=1)[CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].CC1C=CC(S(O[CH2:38][CH:39]2[CH2:48][C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[O:41][CH2:40]2)(=O)=O)=CC=1>>[O:41]1[C:42]2[C:47](=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:48][CH:39]([CH2:38][O:26][C:22]2[CH:21]=[C:20]([C@H:9]([OH:8])[CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:25]=[CH:24][CH:23]=2)[CH2:40]1

Participants

4

Reactant 3

HCID 996PhenolHCID 11267124Toluene-4-sulfonic acid Chroman-3-ylmethyl esterHCID 90405310(R)-tert-butyl 3-hydroxy-3-(3-hydroxyphenyl)propylcarbamate

Product 1

HCID 131733443HCID 131733443, compound

Procedure

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).

Sources & evidence

ORD record
ord-41d3e2f27cc84e85b4cbde620b42cd53
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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