Phenol → HCID 90406404, compound

HRID 2277073Notes

Reaction equation

HRID 2277073 reaction equation
[O:1]=[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[CH:7]=1)[CH2:3][C:4]#[N:5].C1(O)C=CC=CC=1.O[C@@H](C1C=CC=C(O)C=1)CCNC(=O)OC(C)(C)C>>[OH:1][C@@H:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[CH:7]=1)[CH2:3][C:4]#[N:5]

Participants

4

Reactant 3

HCID 996PhenolHCID 90405310(R)-tert-butyl 3-hydroxy-3-(3-hydroxyphenyl)propylcarbamateHCID 90405419HCID 90405419, compound

Product 1

HCID 90406404HCID 90406404, compound

Procedure

Chiral reduction of 3-oxo-3-(3-(thiophen-2-ylmethoxy)phenyl)propanenitrile following the method used in the preparation of phenol (7, Intermediate I) gave after flash column chromatography (R)-3-hydroxy-3-(3-(thiophen-2-ylmethoxy)phenyl)propanenitrile as a white solid. Yield (2.6 g, 82%); 1H NMR (400 MHz, DMSO-d6): δ 7.55 (d, J=4.8 Hz, 1H), 7.25 (t, J=8.0 Hz, 1H), 7.21 (d, J=3.2 Hz, 1H), 7.06-6.99 (m, 3H), 6.94 (dd, J=8.0, 2.0 Hz, 1H), 5.95 (d, J=4.4 Hz, 1H), 5.27 (s, 2H), 4.85 (dd, J=11.2, 4.8 Hz, 1H), 2.92-2.77 (m, 2H). Yield (2.6 g, 92%); MS: m/z 260.06 [M+H]+.

Sources & evidence

ORD record
ord-00a6fbcfea6e4adbaa049fcb4d05f236
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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