1-Ethynylcyclobutan-1-ol → Tert-butyl 3-hydroxy-3-(3-(2-(1-hydroxycyclobutyl)ethynyl)phenyl)propylcarbamate

HRID 1021115Notes

Reaction equation

HRID 1021115 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]([OH:19])[CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:5]=[CH:6][CH:7]=1.[C:20]([C:22]1([OH:26])[CH2:25][CH2:24][CH2:23]1)#[CH:21]>>[OH:19][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:21]#[C:20][C:22]2([OH:26])[CH2:25][CH2:24][CH2:23]2)[CH:3]=1)[CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

3

Reactant 2

HCID 225974291-Ethynylcyclobutan-1-olHCID 57608439Tert-butyl 3-(3-bromophenyl)-3-hydroxypropylcarbamate

Product 1

HCID 66629363Tert-butyl 3-hydroxy-3-(3-(2-(1-hydroxycyclobutyl)ethynyl)phenyl)propylcarbamate

Procedure

Sonogashira reaction of 39 with 1-ethynyl-cyclobutanol yielded tert-butyl 3-hydroxy-3-(3-(2-(1-hydroxycyclobutyl)ethynyl)phenyl)propylcarbamate as yellow oil. Yield (1.5 g, 70%): 1H NMR (400 MHz, DMSO-d6) δ 7.45 (s, 1H), 7.27-7.34 (m, 3H), 4.85 (bs, 1H), 4.71 (m, 1H), 3.48-3.51 (m, 2H), 3.14-3.16 (m, 1H), 2.50-2.52 (m, 2H), 2.30-2.49 (m, 3H), 1.80-1.90 (m, 4H), 1.45 (s, 9H).

Sources & evidence

ORD record
ord-e4b1d516147d4bbf9109f53ce67b722c
Source dataset
uspto-grants-2014_05
Patent number
US08716529B2

Reaction notes

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